Skip to main content

Abstract

The D-vitamins are a group of fat soluble materials with high antirachitic activity. Rickets is a disease of infancy caused by faulty calcium hydroxy apatite deposition in the growing bone. It was Palm (140) in 1890 who found that the disease responded favorably to irradiation of patient’s food or skin by sunlight or ultraviolet light. Mellanby (113) in 1919 first reported the presence of an antirachitic factor in cod-liver oil. This discovery encouraged research on the isolation of the active principle in fish-liver oil, but the low natural concentration of the vitamin made isolation very difficult.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Aberhart, D.J., J.Y.R. Chu, and A.C.T. Hsu: Synthesis of 3-Epicholecalciferol. J. Organ. Chem. (U.S. A.) 41, 1067–1069 (1976).

    Article  CAS  Google Scholar 

  2. Aberhart, D.J., and A.C.T. Hsu: Studies on the Adduct of 4-Phenyl-l,2,4-triazoline-3,5-dione with Vitamin D3. J. Organ. Chem. (U.S.A.) 41, 2098 (1976).

    Article  CAS  Google Scholar 

  3. Abillon, E., and R. Mermet-Bouvier: Effect of Wavelength on Production of Previtamin D2. J. Pharm. Sci. 62, 1688 (1973).

    Article  CAS  Google Scholar 

  4. Ahmad, R., D. Hands, S.L. Leung, J.M. Midgley, H. Safwat, and W.B. Whalley: Unsaturated Steroids. Part 8. Synthesis of Ergosta-5,7-diene-lα,3β-diol, the 4,4-Dimethyl Analogue, and 4,4-Dimethylergosta-5,7-dien-3β-ol. J. Chem. Soc. Perkin I 1978, 74.

    Article  Google Scholar 

  5. Anagnostopoulos, CE., and L.F. Fieser: Nitration of Unsaturated Steroids. J. Amer. Chem. Soc. 76, 532 (1954).

    Article  CAS  Google Scholar 

  6. Askew, S.A., H.M. Bourdillon, H.M. Bruce, R.K. Callow, S.T. Philpot, and T.A. Webster: Crystalline vitamin D. Proc. Roy. Soc. (B) 109, 488 (1932).

    CAS  Google Scholar 

  7. Atkins, D.: A Possible Role of 24,25-Dihydroxycholecalciferol in Bone Resorption. Proc. Soc. Endocr. 144, 28 P (1976).

    Google Scholar 

  8. Bakker, S.A., J. Lugtenburg, and E. Havinga: Studies on Vitamin D and Related Compounds XXII. New Reactions and Products in Vitamin D3 Photochemistry. Rec. Trav. Chim. Pays-Bas 91, 1459 (1972).

    Article  CAS  Google Scholar 

  9. Barrett, A.G.M., D.H.R. Barton, and R.A. Russell: Structure of the Toxisterols: X-Ray Crystal Structure of Toxisterol2-D Epoxide. J. Chem. Soc. Chem. Comm. 1976, 659.

    Google Scholar 

  10. Barrett, A.G.M., D.H.R. Barton, R.A. Russell, and D.A. Widdowson: Photochemical Transformations. Part 34. Structures of the Toxisterols. J. Chem. Soc. Perkin I 1977, 631.

    Article  Google Scholar 

  11. Barton, D.H.R., A. Gunatilaka, T. Nakanishi, H. Patin, D.A. Widdowson, and B.R. Worth: Synthetic Uses of Steroidal Ring B Diene Protection: 22,23-Dihydro- ergosterol. J. Chem. Soc. Perkin I 1976, 821.

    Article  Google Scholar 

  12. Barton, D.H.R., R.H. Hesse, M.M. Pechet, and E. Rizzardo: A Convenient Synthesis of lα-Hydroxy-Vitamin D3. J. Amer. Chem. Soc. 95, 2748 (1973).

    Article  CAS  Google Scholar 

  13. Barton, D.H.R., R.H. Hesse, E. Rizzardo: Convenient Synthesis of Crystalline lα, 25-Dihydroxyvitamin D3. J. Chem. Soc. Chem. Comm. 1974, 203.

    Google Scholar 

  14. Barton, D.H.R., and H. Patin: Chemistry of the Tricarbonyliron Complexes of Calciferol and Ergosterol. J. Chem. Soc. Perkin I 1976, 829.

    Article  Google Scholar 

  15. Barton, D.H.R., T. Shioiri, and D.A. Widdowson: Biosynthesis of Terpenes and Steroids. Part V. The Synthesis of Ergosta-5, 7, 22, 24 (28)-tetraen-3β-ol, a Biosynthetic Precursor of Ergosterol. J. Chem. Soc. (C) 1971, 1968.

    Google Scholar 

  16. Baum, J., F. Holden, M. Roginsky, M.I. Cohen, and L. Finberg: 25-Hydroxy-cholecalciferol in the Management of Rickets Associated with Extra-hepatic Bilary Atresia. J. Pediatrics 88, 1041 (1976).

    Article  Google Scholar 

  17. Blunt, J.W., H.F. Deluca, and H.K. Schnoes: 25-Hydroxycholesterol: A Biologically Active Metabolite of Vitamin D3. Biochemistry 7, 3317 (1968).

    Article  CAS  Google Scholar 

  18. Bolton, I.J., R.G. Harrison, and B. Lythgoe: Calciferol and its Relatives. Part XIV. Total Synthesis of Des-AB-cholestane-8β, 9α-diol (1β-[(1R)-1, 5-Dimethylhexyl] 7αβ-methyl-trans-perhydroindane 4β, 5α-diol). J. Chem. Soc. (C) 1971, 2950.

    Google Scholar 

  19. Bolton, I.J., R.G. Harrison, B. Lythgoe, and R.S. Manwaring: Calciferol and its Relatives. Part XIII. Derivatives ofEnantiomeric-4-methylhex-3-ene-l, trans-2-diols. J. Chem. Soc. (C) 1971, 2944.

    Google Scholar 

  20. Bontekoe, J.S., A. Wignall, M.P. Rappoldt, and J.R. Roborgh: Hydroxylated Vitamin D Analogues. Internat. J. Vit. Res. 40, 589 (1970).

    CAS  Google Scholar 

  21. Boomsma, F., H.J.C. Jacobs, E. Havinga, and A. van der Gen: The “Overirradiation Products” of Previtamin D and Tachysterol: Toxisterols. Rec. Trav. Chim. Pays-Bas 96, 104 (1977).

    Article  CAS  Google Scholar 

  22. Boomsma, F., H.J.C. Jacobs, E. Havinga, and A. van der Gen: Vitamin D and Compounds. XXIII. Structure of Bis (cholestadienol) isomers. Rec. Trav. Chim. Pays-Bas 92, 1361 (1973).

    Article  Google Scholar 

  23. Bordier, P., M.M. Peghet, R. Hesse, P. Marie, and H. Rosenson: Response of Adult Patients with Osteomalacia to Treatment with Crystalline 1 α-Hydroxyvitamin D3. New Engl. J. Med. 291, 866 (1974).

    Article  CAS  Google Scholar 

  24. Boris, A., J.F. Hurley, and T. Trimal: Relative Activities of Some Metabolites and Analogs of Cholecalciferol in Stimulation of Tibia Ash Weight in chicks otherwise deprived of vitamin DJ. Nutr. 107, 194 (1977).

    CAS  Google Scholar 

  25. Boyle, I.T., R.W. Gray, and H.F. Deluca: Regulation by calcium of in vivo Synthesis of 1, 25-Dihydroxycholecalciferol and 21, 25-Dihydroxycholecalciferol. Proc. Nat. Acad. Sci. (U.S.A.) 68, 2131 (1971).

    Article  CAS  Google Scholar 

  26. Boyle, I.T., L. Miravet, R.W. Gray, M.F. Holick, and H.F. Deluca: The Response of Intestinal Calcium Transport to 24-Hydroxy and lα, 25-Dihydroxy- vitamin D in Nephrectomized Rats. Endocrin. 90, 605 (1972).

    Article  CAS  Google Scholar 

  27. Boyle, I.T., J.L. Omdahl, R.W. Gray, and H.F. Deluca: The Biological Activity and Metabolism of 24, 25-Dihydroxyvitamin D3. J. Biol. Chem. 248, 4174 (1973).

    CAS  Google Scholar 

  28. Brickman, A.S., J.W. Coburn, and A.W. Norman: Action of 1, 25-dihydroxy-cholecalciferol, A Potent Kidney Produced Metabolite of Vitamin D3 in Uremic Man. New Engl. J. Med. 287, 891 (1972).

    Article  CAS  Google Scholar 

  29. Brockman, H., and A. Busse: Crystalline Vitamin D from Tuna Fish Liver Oil. Naturwiss. 26, 122 (1938).

    Article  Google Scholar 

  30. Brynjolffssen, J., J.M. Midgley, and W.B. Whalley: Unsaturated Steroids. Part 4. Some Steroidal Hydroxy-4, 4-dimethyl-5, 7-dienes and 4, 4-Dimethyl-5, 7, 14 (15)-trienes. J. Chem. Soc. Perkin I 1977, 812.

    Article  Google Scholar 

  31. Caglioti, L., P. Grasselli, and G. Maina: Modification of the Bamford-Stevens Reaction: A New Route to 7-Dehydrocholesterol. Chim. Ind. (Milan) 45, 559 (1963).

    CAS  Google Scholar 

  32. Chalmers, P.M., N.W. Davies, J.O. Hunter, K.F. Szaz, B. Pelc, and E. Kodicek: lα-Hydroxycholatecalciferol as a Substitute for the Kidney Hormone 1, 25-Dihydroxy- cholecalciferol in Chronic Renal Failure. Lancet 2, 696 (1973).

    Article  CAS  Google Scholar 

  33. Chan, J.C.N., S.B. Olden, M.F. Foley, and H.F. Deluca: lα-Hydroxyvitamin D3 in Chronic Renal Failure. J. Amer. Med. Assoc. 234, 47 (1975).

    Article  CAS  Google Scholar 

  34. Chapelo, C.B., P. Hallett, B. Lythgoe, I. Waterhouse, and P.W. Wright: Calciferol and its Relatives. Part 19. Synthetic Applications of Cyclic Orthoesters: Stereospecific Synthesis of a Bicyclic Alcohol Related to the Vitamins D.J. Chem. Soc. Perkin I 1977, 1211.

    Google Scholar 

  35. Cohen, Z., E. Keinan, Y. Mazur, and A. Ulman: Hydroxylation with Ozone on Silica Gel. The Synthesis of 1, 25-Dihydroxyvitamin D3. J. Organ. Chem. (U.S.A.) 41, 2651 (1976).

    Article  CAS  Google Scholar 

  36. Cork, D.J., M.R. Haussler, M.J. Pitt, E. Rizzardo, R.H. Hesse, and M.M. Pechet: lα-Hydroxyvitamin D3: A Synthetic Sterol which is Highly Active in Preventing Rickets. Endocrin. 94, 1337 (1974).

    Article  CAS  Google Scholar 

  37. Corradino, R.A.: Embryonic chicken testing in organ culture: Response to Vitamin D3 and its Metabolites. Science 179, 402 (1973).

    Article  CAS  Google Scholar 

  38. Dasgupta, S.K., D.R. Crump, and M. Gut: New Preparation of Desmosterol. J. Organ. Chem. (U.S.A.) 39, 1658 (1975).

    Article  Google Scholar 

  39. Dauben, W.G., and P. Bauman: Photochemical Transformations. IX. Total Structure of Suprasterol II. Tetrahedron Lett. 1961, 565.

    Google Scholar 

  40. Dauben, W.G., and G.J. Fonken: The Structure of Photoisopyrocalciferol and Photopyrocalciferol. J. Amer. Chem. Soc. 81, 4060 (1959).

    Article  CAS  Google Scholar 

  41. Dauben, W.G., and D.S. Fullerton: Steroids with Abnormal Internal Configuration. A Stereospecific Synthesis of 8α-Methyl Steroids. J. Organ. Chem. (U. S. A.) 36, 3277 (1971).

    Article  CAS  Google Scholar 

  42. Davidson, R.S., S.M. Waddington-Feather, D.H. Williams, and B. Lythgoe: Calciferol and its Relatives. Part IX. The Synthesis of Tachysterol3. J. Chem. Soc. (C) 1967, 2534; Tetrahedron Lett. 1963, 1413.

    Google Scholar 

  43. Dawson, M.T., J. Dixon, P.S. Littlewood, and B. Lythgoe: Calciferol and its Relatives. Part XII. (S)-3-Ethynyl-4-methylcyclohex-3-en-l-ol. J. Chem. Soc. (C) 1971, 2352.

    Google Scholar 

  44. Dawson, T.M., J. Dixon, P.S. Littlewood, B. Lythgoe, and A.K. Saksena: Calciferol and its Relatives. Part XVI. Total Synthesis of Precalciferols. J. Chem. Soc. (C) 1971, 2960.

    Google Scholar 

  45. Diem, K.: Documenta Geigy. Scientific Tables. New York: Geigy Pharmaceuticals, Ardsley.

    Google Scholar 

  46. Dixon, J., B. Lythgoe, I.A. Siddiqui, and J. Tideswell: Calciferol and its Relatives. Part XI. Improved Routes to (S)-3-Hydroxymethyl-4-methylcyclohex-3-en-l-ol. J. Chem. Soc. (C) 1971, 1301.

    Google Scholar 

  47. Doxiadis, S.A., and PD. Lapatsanis: lα-Hydroxyvitamin D in Neonatal Hypocalcaemia. Lancet 1, 426 (1977).

    Article  CAS  Google Scholar 

  48. Ebel, J.G., A.N. Taylor, and R.H. Wassermann: Vitamin D Induced Calcium Binding Protein of Intestinal Mucosa. Amer. J. Clin. Nutr. 22, 431 (1969).

    CAS  Google Scholar 

  49. Emke, A., D. Hands, J.M. Midgley, WB. Whalley, and R. Ahmad: Unsaturated steroids. Part 6. A Route to Cholesta-5, 7-diene-lα, 3β-diol; Preparation of Steroidal 4,6,8(14)-Trienes. J. Chem. Soc. Perkin I 1977, 820.

    Google Scholar 

  50. Emtage, J.S., D.E.M. Lawson, and E. Kodicek: The Response of the Small Intestine to Vitamin D. Biochem. J. 144, 339 (1974).

    CAS  Google Scholar 

  51. Evans, I.M.A., M. Boulton-Jones, F.H. Doyle, G.F. Jocwin, M. Lockwood, E.W. Matthews, and I. MacIntyre: The Clinical Use of 1,25-Dihydroxychole-calciferol. Proceedings of XI European Symposium on Calcified Tissues. Elsinore, Denmark, 1976, 236.

    Google Scholar 

  52. Eyley, S.C., and D.H. Williams: Photolytic Production of Vitamin D. The Preparative Value of a Photosensitiser. J. Chem. Soc. Chem. Comm. 1975, 858.

    Google Scholar 

  53. Eyley, S.C., and D.H. Williams: Synthesis of 24ε, 25-Dihydroxypro vitamin D3. J. Chem. Soc. Perkin I 1976, 727.

    Article  Google Scholar 

  54. Eyley, S.C., and D.H. Williams: Synthesis of 25-Hydroxyprovitamin D3 and 25ε,26-dihydroxyprovitamin D3. J. Chem. Soc. Perkin I 1976, 731.

    Article  Google Scholar 

  55. Fischer, M.: Industrial Applications of Photochemical Syntheses. Angew. Chem. Int. Ed. 17, 16 (1978).

    Article  Google Scholar 

  56. Fraser, D.R., and E. Kodicek: Unique Biosynthesis by Kidney of a Biologically Active Vitamin D Metabolite. Nature 228, 764 (1970).

    Article  CAS  Google Scholar 

  57. Freeman, D., A. Acher, and Y. Mazur: Synthesis of lα-Hydroxypro vitamin D3. Tetrahedron Lett. 1975, 261.

    Google Scholar 

  58. Freund, T., and F. Bronner: Stimulation in vitro by 1, 25-Dihydroxyvitamin D3 of Intestinal Cell Calcium Uptake and Calcium Binding Protein. Science 190, 1300 (1975).

    Article  CAS  Google Scholar 

  59. Fürst, A., L. Labler, W. Meier, and K.-H. Pfoertner. Synthesis of lα-Hydroxy-cholecalciferol. Helv. Chim. Acta 56, 1708 (1973).

    Article  Google Scholar 

  60. Georghiou, P.E.: The Chemistry of “Vitamin” D: The Hormonal Calciferols. Chem. Soc. Rev. 6, 83 (1977).

    Article  CAS  Google Scholar 

  61. Georghiou, P.E., and G. Just. Cycloadducts of Ergosterol with Azo-type Dienophiles, and their Chemical Reactivities. J. Chem. Soc. Perkin I 1973, 888.

    Article  Google Scholar 

  62. Gray, R.W., H.P. Weber, J.H. Dominquez, and J. Lemann. The Metabolism of Vitamin D3 and 25-Hydroxyvitamin D3 in Normal and Anephric Humans. J. Clin. Endocr. Metab. 39, 1045 (1974).

    Article  CAS  Google Scholar 

  63. Harmeyer, J., and H.F. Deluca: Calcium Binding Protein and Calcium Absorption after Vitamin D Administration. Arch. Biochem. Biophys. 133, 247 (1969).

    Article  CAS  Google Scholar 

  64. Harrison, I.T., and B. Lythgoe: Calciferol and its Relatives. Part III. Partial Synthesis of Calciferol and of Epicalciferol. J. Chem. Soc. ( London ) 1958, 837.

    Google Scholar 

  65. Harrison, R.G., B. Lythgoe, and P.W. Wright: Calciferol and its Relatives. Part XVIII. Total Synthesis of lα-Hydroxyvitamin D3. J. Chem. Soc. Perkin I 1974, 2654.

    Google Scholar 

  66. Haussler, MR.: Vitamin D3 Metabolism, Mode of Action, and Assay of Circulating Hormonal Form. In: Vitamin D and Problems Related to Uremic Bone Disease (Norman, A.W., ed.), p. 25. Berlin: Walter de Gruyter and Co. 1975.

    Google Scholar 

  67. Haussler, M.R., D.W. Boyle, E.T. Littledike, and H. Rasmussen: A Rapidly Acting Metabolite of Vitamin D3. Proc. Nat. Acad. Sci. (U.S.A.) 68, 177 (1971).

    Article  CAS  Google Scholar 

  68. Haussler, M.R., J.F. Myrtle, and A.W. Norman: The Association of a Metabolite of Vitamin D3 with Intestinal Mucosa Chromatin in vivo. J. Biol. Chem. 243, 4055 (1968).

    CAS  Google Scholar 

  69. Haussler, M.R., J.E. Verwekh, R.H. Hesse, E. Rizzardo, and MM. Pechet: Biological Activity of lα-Hydroxycholecalciferol, A Synthetic Analogue of the Hormonal Form of Vitamin D3. Proc. Nat. Acad. Sci. (U.S.A.) 70, 2248 (1973).

    Article  CAS  Google Scholar 

  70. Havinga, E.: Vitamin D, Example and Challenge (Review). Experientia 29, 1181 (1973).

    Article  CAS  Google Scholar 

  71. Henderson, RG., J.G.E. Levinghaf, D.O. Oliver, R. Smith, R.J. Wolton, D.J. Small, C. Preston, G.T. Warner, and A.W. Norman: Effects of 1,25-Dihydroxycholecalciferol on Calcium Absorption, Muscle Weakness and Bone Disease in Chronic Renal Failure. Lancet I, 379 (1974).

    Article  Google Scholar 

  72. Hess, A.F., and M.B. Gutman: The Cure of Infantile Rickets with Sunlight. J. Amer. Med. Assoc. 78, 29 (1922).

    Article  Google Scholar 

  73. Hielbron, I.M., R.N. Jones, K.M. Samant, and F.S. Spring: Studies in the Sterol Group, Part XXIV. The Constitution of Calciferol. J. Chem. Soc. ( London ), 1936, 905.

    Google Scholar 

  74. Hill, L.F., M. Davies, C. M. Taylor, and S. W. Stanbury: Treatment of Hyperparathyroidism with 1,25-Dihydroxycholecalciferol. Clin. Endocrinol. 5, 167S (1976).

    Article  Google Scholar 

  75. Holick, M.F., M. Garabedian, H.K. Schnoes, and H.F. Deluca: Relationship of 25-Hydroxyvitamin D3 Side Chain Structure to Biological Activity. J. Biol. Chem. 250, 226 (1975).

    CAS  Google Scholar 

  76. Holick, M.F., A. Kleiner-Bosallier, H.K. Schnoes, P.M. Kasten, I.T. Boyle, and H.F. Deluca: 1,24,25-Trihydroxyvitamin D3. J. Biol. Chem. 248, 6691 (1973).

    CAS  Google Scholar 

  77. Holick, M.F., H.K. Schnoes, H.F. Deluca, T. Suda, and R.J. Cousins: Isolation and Identification of 1,25-Dihydroxycholecalciferol: A Metabolite of Vitamin D Active in the Intestine. Biochemistry 10, 2799 (1971).

    Article  CAS  Google Scholar 

  78. Holick, M.F., E.J. Semmler, H.K. Schnoes, and H.F. Deluca: lα-Hydroxy Derivative of Vitamin D3: A Highly Potent Analogue of lα,25-Dihydroxyvitamin D3. Science 180, 190 (1973).

    Article  CAS  Google Scholar 

  79. Hunziker, F., and F.X. Müllner: Dehydrohalogenierung mit Trialkylphosphiten: Neue Methode zur Herstellung von 7-Dehydrocholesterin. Helv. Chim. Acta 41, 70 (1958).

    Article  CAS  Google Scholar 

  80. Ikan, R., A. Markus, and Z. Goldschmidt: Synthesis of Steroidal Cyclopropanes. J. Chem. Soc. Perkin I 1972, 2423.

    Article  Google Scholar 

  81. Ikekawa, N., M. Motisaki, N. Koizumi, Y. Kato, and T. Takeshita: Synthesis of active forms of vitamin D. VIII. Synthesis of [24R]- and [24S]-lα,24,25-trihydroxy-vitamin D3. Chem. Pharm. Bull. 23, 695 (1975).

    Article  CAS  Google Scholar 

  82. Inhoffen, H.H., and K. Irmscher: Fortschritte der Chemie der Vitamine D und ihrer Abkömmlinge (Review). Fortschr. Chem. organ. Naturstoffe 17, 70 (1959).

    CAS  Google Scholar 

  83. Inhoffen, H.H., K. Irmscher, H. Hirschfield, U. Stäche, and A. Kreutzer: Partial Synthese der Vitamine D2 und D3. Chem. Ber. 91, 2309 (1958).

    Article  CAS  Google Scholar 

  84. Jacobs, H.J.C., F. Boomsma, E. Havinga, and A. van der Gen: The Photochemistry of Previtamin D and Tachysterol. Rec. Trav. Chim. Pays-Bas 96, 113 (1977).

    Article  CAS  Google Scholar 

  85. Johnson, R.L., S.C. Carey, A.W. Norman, and W.H. Okamura: Studies on Vitamin D and Its Analogues. 10. Side Chain Analogues of 25-Hydroxyvitamin D3. J. Med. Chem. 20, 5 (1977).

    Article  CAS  Google Scholar 

  86. Johnson, R.L., W.H. Okamura, and A.W. Norman: Mode of Action of Calciferol. X. 24-Nor-23-hydroxyvitamin D3, An Analog of 25-Hydroxyvitamin D3 Having Antivitamin Activity. Biochem. Biophys. Res. Comm. 67, 797 (1975).

    Article  CAS  Google Scholar 

  87. Juttmann, J.R., J.D. Baths, and J.C. Birkenhager: Treatment of Anticonvulsant Osteomalacia with lα-Hydroxycholecalciferol. Brit. Ned. J. 1977, 551.

    Google Scholar 

  88. Kaminski, J.J., and N. Bodor: 3-Bromo-4,4-dimethyloxazolidinone, Preparation and Investigation of a New Brominating Agent. Tetrahedron 32, 1097 (1976).

    Article  CAS  Google Scholar 

  89. Kaneko, C., A. Sugimoto, Y. Eguchi, S. Yamada, and M. Ishikawa: A New Synthetic Method of lα-Hydroxy-7-dehydrocholesterol. Tetrahedron 30, 2701 (1974).

    Article  CAS  Google Scholar 

  90. Kaneko, C., S. Yamada, A. Sugimoto, Y. Eguchi, M. Ishikawa, T. Suda, M. Suzuki, S. Kakuta, and S. Sasaki: Synthesis and Biological Activity of la-Hydroxyvitamin D3. Steroids 23, 75 (1974).

    Article  CAS  Google Scholar 

  91. Kaneko, C., S. Yamada, A. Sugimoto, M. Ishikawa, S. Sasaki, and T. Suda: lα-Hydroxylation of Cholesterol and the Related 3-Hydroxysteroids. Tetrahedron Lett. 1973, 2339.

    Google Scholar 

  92. Kaupp, G.: Photochemical Rearrangements and Framentations of Alkenes and Polyenes. Angew. Chem. Int. Ed. 17, 150 (1978).

    Article  Google Scholar 

  93. Kodicek, E.: The Biosynthesis of C14-Labelled Ergocalciferol. Biochem. J. 60, XXV (1955).

    CAS  Google Scholar 

  94. Kodicek, E., D.E.M. Lawson, and P.W. Wilson: Biological Activity of a Polar Metabolite of Vitamin D3. Nature 228, 763 (1970).

    Article  CAS  Google Scholar 

  95. Koizumi, N., M. Morisaki, and N. Ikekawa: Absolute Configurations of 24-Hydroxy-cholesterol and Related Compounds. Tetrahedron Lett. 1975, 2203.

    Google Scholar 

  96. Kooh, S., W.D. Fraser, R. Toon, and H.F. Deluca: Response of Protracted Neonatal Hypocalcaemia to lα, 25-Dihydroxyvitamin D3. Lancet II, 1105 (1976).

    Article  Google Scholar 

  97. Lam, H.-Y., B.L. Onisko, H.K. Schnoes, and H.F. Deluca: Synthesis and Biological Activity of 3-Deoxy-lα-hydroxyvitamin D3. Biochem. Biophys. Res. Comm. 59, 845 (1974).

    Article  CAS  Google Scholar 

  98. Lam, H.-Y., H.K. Schnoes, and H.F. Deluca: Synthesis and Biological Activity of 25ε, 26-Dihydroxycholecalciferol. Steroids 25, 247 (1975).

    Article  CAS  Google Scholar 

  99. Lam, H.-Y., H.K. Schnoes, and H.F. Deluca: Synthesis of lα-Hydroxyergocalciferol. Steroids 30, 671 (1977).

    Article  CAS  Google Scholar 

  100. Lawson, D.E.M.: Abstracts. Third Workshop on Vitamin D, California, 64 (1977).

    Google Scholar 

  101. Lawson, D.E.M., D.R. Fraser, E. Kodicek, H.R. Morris, and D.H. Williams: Identification of 1,25-Dihydroxycholecalciferol, A New Kidney Hormone Controlling Calcium Metabolism. Nature 230, 228 (1971).

    Article  CAS  Google Scholar 

  102. Lawson, D.E.M., P.W. Wilson, and E. Kodicek: New Vitamin D Metabolite Localized in Intestinal Cell Nuclei. Nature 222, 171 (1969).

    Article  CAS  Google Scholar 

  103. Metabolism of Vitamin D: A new Cholecalciferol Metabolite Involving Loss of Hydrogen at C-l in Chick Intestinal Nuclei. Biochem. J. 115, 269 (1969).

    Google Scholar 

  104. Littlewood, P.S., B. Lythgoe, and A.K. Saksena: Calciferol and its Relatives. Part XV. The preparation of Des-AB-cholest-8-ene-8-carbaldehyde {1 β-[(lR)-l,5-Dimethylhexyl]-3 a α, 6,7,7a β-tetrahydro-7a-methylindane-4-carbaldehyde} and 9α-Chloro-des-AB-cholestan-8-one {5 α-Chloro-1β-[(1R)-1,5-dimethylhexyl]-7aβ-methyl-trans-perhydroindan-4-one}. J. Chem. Soc. (C) 1971, 2956.

    Google Scholar 

  105. Long, R.G., K. Skinner, M.R. Wells, and S. Sherlock: Serum 25-Hydroxyvitamin D and Untreated Parenchymal and Cholestatic Liver Disease. Lancet 2, 650 (1976).

    Article  CAS  Google Scholar 

  106. Lund, B., L. Hjorth, I. Kjaer, I. Reimann, T. Friis, R.B. Anderson, and O.H. Sorenson: Treatment of Osteoporosis of Aging with lα-Hydroxycholatecalciferol. Lancet 2, 1168 (1975).

    Article  CAS  Google Scholar 

  107. Lythgoe, B., R. Manwaring, J.R. Milner, TA. Moran, M.E.N. Nambudiry, and J. Tideswell: Calciferol and its Relatives. Part 21. A Synthesis of (S)-(Z)-2-(5-Hydroxy-2 methylenecyclohexylidene)ethanol. J. Chem. Soc. Perkin I 1978, 387.

    Article  Google Scholar 

  108. Lythgoe, B., ME. Nambudiry, and J. Tideswell: Direct Total Synthesis of Vitamins D2 and D3. Tetrahedron Lett. 1977, 3685.

    Google Scholar 

  109. Lythgoe, B., DA. Roberts, and I. Waterhouse: Calciferol and its Relatives. Part 20. A Synthesis of Windhaus and Grundmann’s C19 Ketone. J. Chem. Soc. Perkin I 1977, 2608.

    Article  Google Scholar 

  110. McCollum, E.V., N. Simmonds, J.E. Becker, and P.G. Shipley: Studies on Experimental Rickets XXI. J. Biol. Chem. 53, 293 (1922).

    CAS  Google Scholar 

  111. McMorris, T.C., and SR. Schow: A Convenient Synthesis of 25-Oxo-27-norcholesteryl Acetate. J. Organ. Chem. (U.S.A.) 41, 3759 (1976).

    Article  CAS  Google Scholar 

  112. McMorris, T.C., S.R. Schow, and G.R. Weike: Evidence for a C-29 Hydroxyl Group in Oogoniol. Tetrahedron Lett. 1978, 335.

    Google Scholar 

  113. Mellanby, E.: An Experimental Investigation of Rickets. Lancet 196, 407 (1919).

    Google Scholar 

  114. Mihailovic, M. Lj., Lj. Lorenc, and V. Pavlovic: A Convenient Synthesis of lα-and 1β-Hydroxycholesterol. Tetrahedron Lett. 1977, 441.

    Google Scholar 

  115. Miravet, L., J.R. Del, M. Carre, M.L. Queille, and P. Bordier: The Biological Activity of Synthetic 25,26-Dihydroxycholecalciferol and 24,25-Dihydroxychole-calciferol in Vitamin D-Deficient Rats. Calcif. Tiss. Res. 21, 145 (1976).

    Article  CAS  Google Scholar 

  116. Morii, H., J. Lund, P. Neville, and HF. Deluca: Biological Activity of a Vitamin D Metabolite. Arch. Biochem. Biophys. 120, 508 (1967).

    Article  CAS  Google Scholar 

  117. Morisaki, M., K. Bannai, and N. Ikekawa: Synthesis of Active Forms of Vitamin D. II. Synthesis of 1α-Hydroxycholesterol. Chem. Pharm. Bull. 21, 1853 (1973).

    Article  CAS  Google Scholar 

  118. Morisaki, M., K. Bannai, and N. Ikekawa: Studies on Steroids. XXXVIII. A New Preparation of 1α-Hydroxycholesterol. Chem. Pharm. Bull. 24, 1948 (1976).

    Article  CAS  Google Scholar 

  119. Morisaki, M., N. Koizumi, and N. Ikekawa: Synthesis of Active Forms of Vitamin D. Part IX. Synthesis of lα,24-Dihydroxycholecalciferol. J. Chem. Soc. Perkin I 1975, 1422.

    Google Scholar 

  120. Morisaki, M., J. Rubio-Lightbourn, and N. Ikekawa: Synthesis of Active Forms of Vitamin D.I. A Facile Synthesis of 25-Hydroxycholesterol. Chem. Pharm. Bull. 21, 457 (1973).

    Article  CAS  Google Scholar 

  121. Morisaki, M., J. Rubio-Lightbourn, N. Ikekawa, and T. Takeshita: Synthesis of Active Forms of Vitamin D. V. A Practical Route to lα,25-Dihydroxycholesterol. Chem. Pharm. Bull. 21, 2568 (1973).

    CAS  Google Scholar 

  122. Morisaki, M., A. Saika, K. Bannai, M. Sawamura, J. Rubio-Lightbourn, and N. Ikekawa. Synthesis of Active Forms of Vitamin D. X. Synthesis of lα-Hydroxy-vitamin D3. Chem. Pharm. Bull. 23, 3272 (1975).

    Article  CAS  Google Scholar 

  123. Mouriño, A., and W.H. Okamura: Studies on Vitamin D and Its Analogues. 14. On the 10,19-Dihydrovitamins Related to Vitamin D2 Including Dihydrotachysterol. J. Organ. Chem. (U.S.A.) 43, 1653 (1978).

    Article  Google Scholar 

  124. Myrtle, J.F., and AW. Norman: Vitamin D: A Cholecalciferol Metabolite Highly Active in Promoting Intestinal Calcium Transport. Science 171, 79 (1971).

    Article  CAS  Google Scholar 

  125. Narwid, T.A., J.F. Blount, J.A. Iacobelli, and M.R. Uskokovic: Vitamin D3 Metabolites. III. Synthesis and X-ray Analysis of lα,25-Dihydroxycholesterol. Helv. Chim. Acta 57, 781 (1974).

    Article  CAS  Google Scholar 

  126. Narwid, T.A., K.E. Cooney, and M.R. Uskokovic: Vitamin D3 Metabolites. II. Further Syntheses of 25-Hydroxycholesterol. Helv. Chim. Acta 57, 771 (1974).

    Article  CAS  Google Scholar 

  127. Norman, A.W.: The Mode of Action of Vitamin D. Biol. Rev. Cambridge Phil. Soc. 43, 97 (1968).

    Article  CAS  Google Scholar 

  128. Norman, A.W., and HF. Deluca: The Preparation of H3-Vitamins D2 and D3 and Their Localization in the Rat. Biochemistry 2, 1160 (1963).

    Article  CAS  Google Scholar 

  129. Norman, A.W., J. Lund, and H.F. Deluca: Biologically Active Forms of Vitamin D3 in the Kidney and Intestine. Arch. Biochem. Biophys. 108, 12 (1964).

    Article  CAS  Google Scholar 

  130. Norman, A.W., J.F. Myrtle, R.J. Midgett, HG. Nowicki, V. Williams, and G. Popjak: 1,25-Dihydroxycholecalciferol: Identification of the Proposed Active Form of Vitamin D3 in the Intestine. Science 173, 51 (1971).

    Article  CAS  Google Scholar 

  131. Ohki, E.: Steroidal Studies. XV. Synthesis of 4,4-Dimethylcholecalciferol and Its Conversion into 10-Isosteroid. Chem. Pharm. Bull. 8, 46 (1960).

    Article  CAS  Google Scholar 

  132. Ochi, K., I. Matsunaga, M. Shindo, and C. Kaneko: Synthesis of Desmosterol and Epidesmosterol from Hyodeoxycholic Acid. Steroids 30, 2204 (1977).

    Article  Google Scholar 

  133. Okamura, W.H., M.L. Hammond, A. Rego, A.W. Norman, and RM. Wing: Studies of 5,6-trans-Vitamin D3 and the Stereoisomers of 10,19-Dihydrovitamin D3 Including Dihydrotachysterol. J. Organ. Chem. (U.S.A.) 42, 2284 (1977).

    Article  CAS  Google Scholar 

  134. Okamura, W.H., M.N. Mitra, M.R. Pirio, A. Mourino, S.C. Carey, and A.W. Norman: Studies on Vitamin D and Its Analogs. 13. 3-Deoxy-3α-methyl-lα-hydroxy-vitamin D3, 3-Deoxy-3α-methyl-lα,25-dihydroxyvitamin D3 and lα-Hydroxy-3-epivitamin D3. Analogues with Conformationally Biased A Rings. J. Organ. Chem. (U.S.A.) 43, 574 (1978).

    Article  CAS  Google Scholar 

  135. Okamura, W.H., M.N. Mitra, R.M. Wing, and A.W. Norman: Chemical Syntheses and Biological Activity of 3-Deoxy-lα-hydroxy vitamin D3 an Analog of lα,25-Di-hydroxyvitamin D3, the Active Form of Vitamin D3. Biochem. Biophys. Res. Comm. 60, 179 (1974).

    Article  CAS  Google Scholar 

  136. Okamura, W.H., and M.R. Pirio: Vitamin D and Its Analogs. IX. lα-Hydroxy-3- epivitamin D3, Its Synthesis and Conformational Analysis. Tetrahedron Lett. 1975, 17.

    Google Scholar 

  137. Onisko, B.L., H.-Y. Lam, L.E. Reeve, H.K. Schnoes, and H.F. Deluca: Synthesis and Bioassay of 3-Deoxy-lα-hydroxyvitamin D3, an Active Analog of lα,25-Di-hydroxyvitamin D3. Bioorg. Chem. 6, 203 (1977).

    Article  CAS  Google Scholar 

  138. Onisko, B.L., H.K. Schnoes, and H.F. Deluca: Synthesis of Potential Vitamin D Antagonists. Tetrahedron Lett. 1977, 1107.

    Google Scholar 

  139. Paaren, H.E., H.K. Schnoes, and H.F. Deluca: Synthesis of 1β-Hydroxyvitamin D3 and 1β, 25-Dihydroxyvitamin D3. a) J. Chem. Soc. Chem. Comm. 1977, 890; b) Proc. Nat. Acad. Sci. (U.S.A.) 75, 2080 (1978).

    Google Scholar 

  140. Palm, T.A.: The Geographical Distribution and Etiology of Rickets. Practitioner 45, 270 (1890).

    Google Scholar 

  141. Partridge, J.J., S. Faber, and M.R. Uskokovic: Vitamin D3 Metabolites. I. Synthesis of 25-Hydroxycholesterol. Helv. Chim. Acta 57, 764 (1974).

    Article  CAS  Google Scholar 

  142. Partridge, J.J., V. Toome, and M.R. Uskokovic: A Stereoselective Synthesis of the 24(R), 25-Dihydroxycholesterol Side Chain. J. Amer. Chem. Soc. 98, 3739 (1976).

    Article  CAS  Google Scholar 

  143. Peacock, M., J.C. Gallagher, and B.E.C. Nordin: Action of lα-Hydroxyvitamin D3 on Calcium Absorption and Bone Resorption in Man. Lancet I, 385 (1974).

    Article  Google Scholar 

  144. Pechet, M.M., and R.H. Hesse: Metabolic and Clinical Effects of Pure Crystalline lα-Hydroxyvitamin D3 and lα,25-Dihydroxyvitamin D3. Amer. J. Med. 57, 13 (1974).

    Article  CAS  Google Scholar 

  145. Pechet, M.M., and R.H. Hesse: The Biological Activities of Pure Crystalline 1α-Hydroxyvitamin D3 and 1α,25-Dihydroxyvitamin D3. Mol. Cell Endo. 1, 305 (1974).

    Article  CAS  Google Scholar 

  146. Pelc, B.: 4β-Hydroxycholecalciferol and an Attempted Synthesis of its 4β-Hydroxy-epimer. J. Chem. Soc. Perkin I 1974, 1436.

    Article  Google Scholar 

  147. Pelc, B.: The Selenium Dioxide Oxidation of Cholecalciferol. Steroids 30, 193 (1977).

    Article  CAS  Google Scholar 

  148. Pelc, B., and E. Kodicek: lα-Hydroxycholesterol. J. Chem. Soc. (C) 1970, 1624.

    Google Scholar 

  149. Pelc, B., and D.H. Marshall: Thermal Transformation of Cholecalciferol Between 100–170°. Steroids 31, 23 (1978).

    Article  CAS  Google Scholar 

  150. Ponchon, G., and H.F. Deluca: The Role of the Liver in the Metabolism of Vitamin D. J. Clin. Invest. 48, 2373 (1969).

    Google Scholar 

  151. Proscal, D.A., H.L. Henry, G.J. Friedlander, and A.W. Norman: Studies on the Mode of Action of Calciferol. Arch. Biochem. Biophys. 179, 229 (1977).

    Article  Google Scholar 

  152. Raisz, L.G., and H.F. Deluca: Effects of Thyrocalcitonin and Phosphate Ion on the Parathyroid Hormone Stimulated Resorption of Bone. Endocrin. 1972, 479.

    Google Scholar 

  153. Redel, J., N. Bazely, Y. Calando, and F. Delbarre: The Synthesis of 24,25-Di-hydroxycholecalciferol, A Metabolite of Vitamin D3. J. Steroid Biochem. 6, 117 (1975).

    Article  CAS  Google Scholar 

  154. Redel, J., P.A. Bell, N. Bazely, Y. Calando, F. Delbarre, and E. Kodicek: The Synthesis and Biological Activity of 25,26-Dihydroxycholecalciferol, A Polar Metaboite of Vitamin D3. Steroids 24, 463 (1974).

    Article  CAS  Google Scholar 

  155. Redel, J., L. Miravet, N. Bazely, Y. Calando, M. Carre, and F. Delbarre: Synthesis and Biological Activity of Diastereoisomers of 25R- and 25S-25,26-Di-hydroxycholecalciferol. Compt. Rend. Acad. Sc. (Paris) D 285, 443 (1977).

    CAS  Google Scholar 

  156. Rotman, A., and Y. Mazur: C-25 Hydroxylation of Cholesterol Derivatives. J. Chem. Soc. Chem. Comm. 1974, 15.

    Google Scholar 

  157. Rubio-Lightbourn, J., M. Morisaki, and N. Ikekawa: Synthesis of Active Forms of Vitamin D. III. Synthesis of lα,25-Dihydroxychoiesterol. Chem. Pharm. Bull. 21, 1854 (1973).

    Article  CAS  Google Scholar 

  158. Russell, R.G.G., R. Smith, R.J. Walton, C. Preston, R. Basson, R.E. Henderson, and A.W. Norman: 1,25-Dihydroxycholecalciferol and lα-Hydroxychole-calciferol in Hyperparathyroidism. Lancet II, 14 (1974).

    Article  Google Scholar 

  159. Salmond, W.G.: Approaches to the Synthesis of Vitamin D Metabolites and Analogs. In: Vitamin D: Biochemical, Chemical and Clinical Aspects Related to Calcium Metabolism (Norman, A.W., K. Schaefer, J.W. Coburn, H.F. Deluca, D. Fraser, H.G. Grigoleit, and D.V. Herrath, eds.), p. 61. Berlin: W. de Gruyter. 1977.

    Google Scholar 

  160. Salmond, W.G., M.A. Barta, A.M. Cain, and M.C. Sobala: Alternative Modes of Decomposition of Allylic Selenoxides Diastereoisomeric at Selenium. Preparation of Δ5,7- and 5 P-Hydroxy-Δ6-steroids. Tetrahedron Lett. 1977, 1683.

    Google Scholar 

  161. Salmond, W.G., M.A. Barta, and J.L. Havens: A Stereoselective Wittig Reagent and Its Application to the Synthesis of 25-Hydroxylated Vitamin D Metabolites. J. Organ. Chem. (U.S.A.) 43, 790 (1978).

    Article  CAS  Google Scholar 

  162. Salmond, W.G., M.A. Barta, and J.L. Havens: Allylic Oxidation with 3,5-Dimethylpyrazole: Chromium Trioxide Complex. Steroidal Δ5, 7-Ketones. J. Organ. Chem. (U. S. A.) 43, 2057 (1978).

    Article  CAS  Google Scholar 

  163. Salmond, W.G., and K.D. Maisto: A Synthesis of 25-Hydroxycholesterol. Tetrahedron Lett. 1977, 987.

    Google Scholar 

  164. Salmond, W.G., and M.C. Sobala: An Efficient Synthesis of 25-Hydroxycholesterol from Stigmasterol. Tetrahedron Lett. 1977, 1695.

    Google Scholar 

  165. Salmond, W.G., M.C. Sobala, and K.D. Maisto: A Synthesis of 25-Hydroxycholesterol. Tetrahedron Lett. 1977, 1237.

    Google Scholar 

  166. Sanders, G.M., J. Pot, and E. Havinga: Some Recent Results in the Chemistry and Stereochemistry of Vitamin D and its Isomers (Review). Fortschr. Chem. organ. Naturstoffe 27, 131 (1969).

    CAS  Google Scholar 

  167. Schnoes, H.K., and H.F. Deluca: Vitamin D: Chemistry and Biochemistry of a New Hormonal System (Review). In: Bioorganic Chemistry, Vol. II (Tamelen, E.E. van, ed.), chap. 12, p. 299. New York: Academic Press. 1978.

    Google Scholar 

  168. Seki, M., N. Koizumi, M. Morisaki, and N. Ikekawa: Synthesis of Active Forms of Vitamin D. VI. Synthesis of (24R)-and (24S)-24,25-Dihydroxyvitamin D3. Tetrahedron Lett. 1975, 15.

    Google Scholar 

  169. Seki, M., J. Rubio-Lightbourn, M. Morisaki, and N. Ikekawa: Synthesis of Active Forms of Vitamin D. IV. Synthesis of 24,25-and 25,26-Dihydroxycholesterol. Chem. Pharm. Bull. 21, 2783 (1973).

    Article  CAS  Google Scholar 

  170. Semmler, E.J., M.F. Holick, H.K. Schnoes, and H.F. Deluca: The Synthesis of lα,25-Dihydroxycholecalciferol — A Metabolically Active Form of Vitamin D3. Tetrahedron Lett 1972, 4147.

    Google Scholar 

  171. Sheves, M., N. Friedman, and Y. Mazur: Conformational Equilibria in Vitamin D. Synthesis of 1β-Hydroxyvitamin D3. J. Organ. Chem. (U.S.A.) 42, 3597 (1977).

    Article  CAS  Google Scholar 

  172. Sheves, M., and Y. Mazur: The Vitamin D-3,5-Cyclovitamin D Rearrangement. J. Amer. Chem. Soc. 97, 6249 (1975).

    Article  CAS  Google Scholar 

  173. Sheves, M., and Y. Mazur: Equilibria in Vitamin D3. Preparation and Properties of 6-Methylvitamin D3 and its Isomers. J. Chem. Soc. Chem. Comm. 1977, 21.

    Google Scholar 

  174. Sheves, M., and Y. Mazur: Epimerization of Vitamin D3. The Cholecalciferyl Ion. Tetrahedron Lett. 1976, 1913.

    Google Scholar 

  175. Silverburg, Z.S., K.B. Bettcher, G.B. Dossetor, T.R. Overton, M.F. Foley, and H.F. Deluca: Effect of 1,25-Dihydroxychoiecakiferol in Renal Osteodystrophy. Can. Med. Ass. J. 112, 190 (1975).

    Google Scholar 

  176. Spencer, R., M. Charman, P. Wilson, and E. Lawson: Vitamin D-Stimulated Intestinal Calcium Absorption May Not Involve Calcium Binding Protein Directly. Nature 263, 161 (1976).

    Article  CAS  Google Scholar 

  177. Stern, P.H., C.L. Trummel, H.K. Schnoes, and H.F. Deluca: Bone Resorbing Activity of Vitamin D Metabolites and Congeners in vitro: Influence of Hydroxyl Substituents in the A-Ring. Endocrin. 97, 1552 (1976).

    Article  Google Scholar 

  178. Strating, J.: Compounds Related to Provitamin D3. IV. 3-Methylcholesterol and the Corresponding Provitamin. Rec. Trav. Chim. Pays-Bas 71, 822 (1952).

    Article  CAS  Google Scholar 

  179. Suda, T., H.F. Deluca, H.K. Schnoes, Y. Tanaka, and M.F. Holick: 25,26-Di-hydrocholecalciferol, A Metabolite of Vitamin D3 with Intestinal Calcium Transport Activity. Biochemistry 9, 4776 (1970).

    Article  Google Scholar 

  180. Takeshita, T., S. Ishimoto, and N. Ikekawa: Preparation of Desmosterol from Fucosterol. Chem. Pharm. Bull. 24, 1928 (1976).

    Article  CAS  Google Scholar 

  181. Tanaka, Y., L. Castillo, H.F. Deluca, and N. Ikekawa: The 24-Hydroxylation of 1,25-Dihydroxyvitamin D3. J. Biol. Chem. 252, 1421 (1977).

    CAS  Google Scholar 

  182. Tanaka, Y., and H.F. Deluca: Biological Activity of 1,25-Dihydroxyvitamin D in the Rat. Endocrin. 92, 417 (1973).

    Article  CAS  Google Scholar 

  183. Tanaka, Y., H.F. Deluca, A. Akaiwa, M. Morisaki, and N. Ikekawa: Synthesis of 24S- and 24R-Hydroxy-[24-3H]-vitamin D3 and their Metabolism in Rachitic Rats. Arch. Biochem. Biophys. 177, 615 (1976).

    Article  CAS  Google Scholar 

  184. Tanaka, Y., H.F. Deluca, N. Loizomi, and N. Ikekawa: Importance of the Stereochemical Position of the 24-Hydroxyl to Biological Activity of 24-Hydroxyvitamin D3 and lα,25-Dihydroxyvitamin D3 on Intestinal Calcium Uptake. Proc. Nat. Acad. Sci. (U.S.A.) 72, 229 (1975).

    Article  Google Scholar 

  185. Trost, B.M., D.F. Taber, and J.B. Alper: An Approach to the Stereocontrolled Creation of an Acyclic Side Chain of Some Natural Products. Tetrahedron Lett. 1976, 3857.

    Google Scholar 

  186. Trost, B.M., and T.R. Verhoeven: New Synthetic Reactions. Catalytic vs. Stoichiometric Allylic Alkylation. Stereocontrolled Approach to Steroid Side Chain. J. Amer. Chem. Soc. 98, 630 (1976).

    Article  CAS  Google Scholar 

  187. Trummel, C.L., L.G. Raisz, and R.B. Hallick: 25-Hydroxydihydrotachysterol — Stimulation of Bone Resorption in Tissue Culture. Biochem. Biophys. Res. Comm. 44, 1096 (1971).

    Article  CAS  Google Scholar 

  188. Tschesche, R., B. Goossens, G. Piestert, and A. Tospfer: Synthesis of 27-Nor-25- oxocholest-5-en-3β-yl Acetate and 27-Nor-25-oxocholestanol from Pregnenolone. Tetrahedron Lett. 1977, 735.

    Google Scholar 

  189. Wagenfeld, J.B., B.A. Nenchausky, M. Bolt, J. Vander Horst, J.L. Boyer, and I.H. Rosenberg: Comparison of Vitamin D and 25-Hydroxyvitamin D in the Therapy of Primary Biliary Cirrhosis. Lancet II, 391 (1976).

    Article  Google Scholar 

  190. Wassermann, R.H.: Mechanism of Intestinal Calcium Absorption. Abstracts, Third Workshop on Vitamin D, California, 1976, 76.

    Google Scholar 

  191. Wicha, J., and K. Bal: Synthesis of 25-Hydroxycholesterol from 3β-Hydroxyandrost-5-en-17-one. A Method for Stereospecific Construction of a Sterol Side-Chain. J. Chem. Soc. Chem. Comm. 1975, 968.

    Google Scholar 

  192. Wicha, J., and K. Bal: Synthesis of Preg-17(20)-en-21-oic Acid Derivatives. Syn. Comm. 7, 215 (1977).

    Article  CAS  Google Scholar 

  193. Windhaus, A., O. Linsert, A. Luttringhaus, and G. Weidlich: Über das kristallisierte Vitamin D2. Ann. 492, 226 (1932).

    Google Scholar 

  194. Windhaus, A., Fr. Schenk, and F. von Werder: Über das antirachitisch wirksame Bestrahlungsprodukt aus 7-Dehydrocholesterin. Z. Physiol. Chem. 241, 100 (1936).

    Article  Google Scholar 

  195. Windhaus, A., and W. Thiele: Über die Konstitution des Vitamin D2. Ann. 521, 160 (1936).

    Google Scholar 

  196. Wong, R.G., J.F. Myrtle, and H.C. Tsai: Studies on Calciferol Metabolism. V. The Occurrance and Biological Activity of 1,25-Dihydroxyvitamin D in Bon. J. Biol. Chem. 247, 5728 (1972).

    CAS  Google Scholar 

  197. Wong, R.G., A.W. Norman, C.R. Reddy, and J.W. Coburn: Biological Effects of 1,25-Dihydroxycholecalciferol (A Highly Active Vitamin D Metabolite) in Acutely Uremic Rats. J. Clin. Invest. 51, 1287 (1972).

    Article  CAS  Google Scholar 

  198. Yakhimovich, R.I., N.F. Fursaeva, and G.M. Segal: Synthesis of the Fluoroanalog of Vitamin D3. Bioorg. Khim. 1976, 1526.

    Google Scholar 

  199. Yang, S.S., C.P. Dorn, and H. Jones: Synthesis of 25-Fluorovitamin D. Tetrahedron Lett. 1977, 2315.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1980 Springer-Verlag/Wien

About this chapter

Cite this chapter

Jones, H., Rasmusson, G.H. (1980). Recent Advances in the Biology and Chemistry of Vitamin D. In: Herz, W., Grisebach, H., Kirby, G.W. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 39. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8551-3_2

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-8551-3_2

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-8553-7

  • Online ISBN: 978-3-7091-8551-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics