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.


Bone Resorption Total Synthesis Intestinal Calcium Absorption Lithium Aluminum Hydride Hydride Reduction 
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  1. 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).CrossRefGoogle Scholar
  2. 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).CrossRefGoogle Scholar
  3. 3.
    Abillon, E., and R. Mermet-Bouvier: Effect of Wavelength on Production of Previtamin D2. J. Pharm. Sci. 62, 1688 (1973).CrossRefGoogle Scholar
  4. 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.CrossRefGoogle Scholar
  5. 5.
    Anagnostopoulos, CE., and L.F. Fieser: Nitration of Unsaturated Steroids. J. Amer. Chem. Soc. 76, 532 (1954).CrossRefGoogle Scholar
  6. 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).Google Scholar
  7. 7.
    Atkins, D.: A Possible Role of 24,25-Dihydroxycholecalciferol in Bone Resorption. Proc. Soc. Endocr. 144, 28 P (1976).Google Scholar
  8. 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).CrossRefGoogle Scholar
  9. 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. 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.CrossRefGoogle Scholar
  11. 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.CrossRefGoogle Scholar
  12. 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).CrossRefGoogle Scholar
  13. 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. 14.
    Barton, D.H.R., and H. Patin: Chemistry of the Tricarbonyliron Complexes of Calciferol and Ergosterol. J. Chem. Soc. Perkin I 1976, 829.CrossRefGoogle Scholar
  15. 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. 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).CrossRefGoogle Scholar
  17. 17.
    Blunt, J.W., H.F. Deluca, and H.K. Schnoes: 25-Hydroxycholesterol: A Biologically Active Metabolite of Vitamin D3. Biochemistry 7, 3317 (1968).CrossRefGoogle Scholar
  18. 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. 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. 20.
    Bontekoe, J.S., A. Wignall, M.P. Rappoldt, and J.R. Roborgh: Hydroxylated Vitamin D Analogues. Internat. J. Vit. Res. 40, 589 (1970).Google Scholar
  21. 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).CrossRefGoogle Scholar
  22. 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).CrossRefGoogle Scholar
  23. 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).CrossRefGoogle Scholar
  24. 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).Google Scholar
  25. 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).CrossRefGoogle Scholar
  26. 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).CrossRefGoogle Scholar
  27. 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).Google Scholar
  28. 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).CrossRefGoogle Scholar
  29. 29.
    Brockman, H., and A. Busse: Crystalline Vitamin D from Tuna Fish Liver Oil. Naturwiss. 26, 122 (1938).CrossRefGoogle Scholar
  30. 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.CrossRefGoogle Scholar
  31. 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).Google Scholar
  32. 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).CrossRefGoogle Scholar
  33. 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).CrossRefGoogle Scholar
  34. 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. 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).CrossRefGoogle Scholar
  36. 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).CrossRefGoogle Scholar
  37. 37.
    Corradino, R.A.: Embryonic chicken testing in organ culture: Response to Vitamin D3 and its Metabolites. Science 179, 402 (1973).CrossRefGoogle Scholar
  38. 38.
    Dasgupta, S.K., D.R. Crump, and M. Gut: New Preparation of Desmosterol. J. Organ. Chem. (U.S.A.) 39, 1658 (1975).CrossRefGoogle Scholar
  39. 39.
    Dauben, W.G., and P. Bauman: Photochemical Transformations. IX. Total Structure of Suprasterol II. Tetrahedron Lett. 1961, 565.Google Scholar
  40. 40.
    Dauben, W.G., and G.J. Fonken: The Structure of Photoisopyrocalciferol and Photopyrocalciferol. J. Amer. Chem. Soc. 81, 4060 (1959).CrossRefGoogle Scholar
  41. 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).CrossRefGoogle Scholar
  42. 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. 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. 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. 45.
    Diem, K.: Documenta Geigy. Scientific Tables. New York: Geigy Pharmaceuticals, Ardsley.Google Scholar
  46. 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. 47.
    Doxiadis, S.A., and PD. Lapatsanis: lα-Hydroxyvitamin D in Neonatal Hypocalcaemia. Lancet 1, 426 (1977).CrossRefGoogle Scholar
  48. 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).Google Scholar
  49. 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. 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).Google Scholar
  51. 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. 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. 53.
    Eyley, S.C., and D.H. Williams: Synthesis of 24ε, 25-Dihydroxypro vitamin D3. J. Chem. Soc. Perkin I 1976, 727.CrossRefGoogle Scholar
  54. 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.CrossRefGoogle Scholar
  55. 55.
    Fischer, M.: Industrial Applications of Photochemical Syntheses. Angew. Chem. Int. Ed. 17, 16 (1978).CrossRefGoogle Scholar
  56. 56.
    Fraser, D.R., and E. Kodicek: Unique Biosynthesis by Kidney of a Biologically Active Vitamin D Metabolite. Nature 228, 764 (1970).CrossRefGoogle Scholar
  57. 57.
    Freeman, D., A. Acher, and Y. Mazur: Synthesis of lα-Hydroxypro vitamin D3. Tetrahedron Lett. 1975, 261.Google Scholar
  58. 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).CrossRefGoogle Scholar
  59. 59.
    Fürst, A., L. Labler, W. Meier, and K.-H. Pfoertner. Synthesis of lα-Hydroxy-cholecalciferol. Helv. Chim. Acta 56, 1708 (1973).CrossRefGoogle Scholar
  60. 60.
    Georghiou, P.E.: The Chemistry of “Vitamin” D: The Hormonal Calciferols. Chem. Soc. Rev. 6, 83 (1977).CrossRefGoogle Scholar
  61. 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.CrossRefGoogle Scholar
  62. 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).CrossRefGoogle Scholar
  63. 63.
    Harmeyer, J., and H.F. Deluca: Calcium Binding Protein and Calcium Absorption after Vitamin D Administration. Arch. Biochem. Biophys. 133, 247 (1969).CrossRefGoogle Scholar
  64. 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. 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. 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. 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).CrossRefGoogle Scholar
  68. 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).Google Scholar
  69. 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).CrossRefGoogle Scholar
  70. 70.
    Havinga, E.: Vitamin D, Example and Challenge (Review). Experientia 29, 1181 (1973).CrossRefGoogle Scholar
  71. 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).CrossRefGoogle Scholar
  72. 72.
    Hess, A.F., and M.B. Gutman: The Cure of Infantile Rickets with Sunlight. J. Amer. Med. Assoc. 78, 29 (1922).CrossRefGoogle Scholar
  73. 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. 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).CrossRefGoogle Scholar
  75. 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).Google Scholar
  76. 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).Google Scholar
  77. 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).CrossRefGoogle Scholar
  78. 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).CrossRefGoogle Scholar
  79. 79.
    Hunziker, F., and F.X. Müllner: Dehydrohalogenierung mit Trialkylphosphiten: Neue Methode zur Herstellung von 7-Dehydrocholesterin. Helv. Chim. Acta 41, 70 (1958).CrossRefGoogle Scholar
  80. 80.
    Ikan, R., A. Markus, and Z. Goldschmidt: Synthesis of Steroidal Cyclopropanes. J. Chem. Soc. Perkin I 1972, 2423.CrossRefGoogle Scholar
  81. 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).CrossRefGoogle Scholar
  82. 82.
    Inhoffen, H.H., and K. Irmscher: Fortschritte der Chemie der Vitamine D und ihrer Abkömmlinge (Review). Fortschr. Chem. organ. Naturstoffe 17, 70 (1959).Google Scholar
  83. 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).CrossRefGoogle Scholar
  84. 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).CrossRefGoogle Scholar
  85. 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).CrossRefGoogle Scholar
  86. 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).CrossRefGoogle Scholar
  87. 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. 88.
    Kaminski, J.J., and N. Bodor: 3-Bromo-4,4-dimethyloxazolidinone, Preparation and Investigation of a New Brominating Agent. Tetrahedron 32, 1097 (1976).CrossRefGoogle Scholar
  89. 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).CrossRefGoogle Scholar
  90. 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).CrossRefGoogle Scholar
  91. 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. 92.
    Kaupp, G.: Photochemical Rearrangements and Framentations of Alkenes and Polyenes. Angew. Chem. Int. Ed. 17, 150 (1978).CrossRefGoogle Scholar
  93. 93.
    Kodicek, E.: The Biosynthesis of C14-Labelled Ergocalciferol. Biochem. J. 60, XXV (1955).Google Scholar
  94. 94.
    Kodicek, E., D.E.M. Lawson, and P.W. Wilson: Biological Activity of a Polar Metabolite of Vitamin D3. Nature 228, 763 (1970).CrossRefGoogle Scholar
  95. 95.
    Koizumi, N., M. Morisaki, and N. Ikekawa: Absolute Configurations of 24-Hydroxy-cholesterol and Related Compounds. Tetrahedron Lett. 1975, 2203.Google Scholar
  96. 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).CrossRefGoogle Scholar
  97. 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).CrossRefGoogle Scholar
  98. 98.
    Lam, H.-Y., H.K. Schnoes, and H.F. Deluca: Synthesis and Biological Activity of 25ε, 26-Dihydroxycholecalciferol. Steroids 25, 247 (1975).CrossRefGoogle Scholar
  99. 99.
    Lam, H.-Y., H.K. Schnoes, and H.F. Deluca: Synthesis of lα-Hydroxyergocalciferol. Steroids 30, 671 (1977).CrossRefGoogle Scholar
  100. 100.
    Lawson, D.E.M.: Abstracts. Third Workshop on Vitamin D, California, 64 (1977).Google Scholar
  101. 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).CrossRefGoogle Scholar
  102. 102.
    Lawson, D.E.M., P.W. Wilson, and E. Kodicek: New Vitamin D Metabolite Localized in Intestinal Cell Nuclei. Nature 222, 171 (1969).CrossRefGoogle Scholar
  103. 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. 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. 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).CrossRefGoogle Scholar
  106. 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).CrossRefGoogle Scholar
  107. 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.CrossRefGoogle Scholar
  108. 108.
    Lythgoe, B., ME. Nambudiry, and J. Tideswell: Direct Total Synthesis of Vitamins D2 and D3. Tetrahedron Lett. 1977, 3685.Google Scholar
  109. 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.CrossRefGoogle Scholar
  110. 110.
    McCollum, E.V., N. Simmonds, J.E. Becker, and P.G. Shipley: Studies on Experimental Rickets XXI. J. Biol. Chem. 53, 293 (1922).Google Scholar
  111. 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).CrossRefGoogle Scholar
  112. 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. 113.
    Mellanby, E.: An Experimental Investigation of Rickets. Lancet 196, 407 (1919).Google Scholar
  114. 114.
    Mihailovic, M. Lj., Lj. Lorenc, and V. Pavlovic: A Convenient Synthesis of lα-and 1β-Hydroxycholesterol. Tetrahedron Lett. 1977, 441.Google Scholar
  115. 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).CrossRefGoogle Scholar
  116. 116.
    Morii, H., J. Lund, P. Neville, and HF. Deluca: Biological Activity of a Vitamin D Metabolite. Arch. Biochem. Biophys. 120, 508 (1967).CrossRefGoogle Scholar
  117. 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).CrossRefGoogle Scholar
  118. 118.
    Morisaki, M., K. Bannai, and N. Ikekawa: Studies on Steroids. XXXVIII. A New Preparation of 1α-Hydroxycholesterol. Chem. Pharm. Bull. 24, 1948 (1976).CrossRefGoogle Scholar
  119. 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. 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).CrossRefGoogle Scholar
  121. 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).Google Scholar
  122. 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).CrossRefGoogle Scholar
  123. 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).CrossRefGoogle Scholar
  124. 124.
    Myrtle, J.F., and AW. Norman: Vitamin D: A Cholecalciferol Metabolite Highly Active in Promoting Intestinal Calcium Transport. Science 171, 79 (1971).CrossRefGoogle Scholar
  125. 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).CrossRefGoogle Scholar
  126. 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).CrossRefGoogle Scholar
  127. 127.
    Norman, A.W.: The Mode of Action of Vitamin D. Biol. Rev. Cambridge Phil. Soc. 43, 97 (1968).CrossRefGoogle Scholar
  128. 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).CrossRefGoogle Scholar
  129. 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).CrossRefGoogle Scholar
  130. 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).CrossRefGoogle Scholar
  131. 131.
    Ohki, E.: Steroidal Studies. XV. Synthesis of 4,4-Dimethylcholecalciferol and Its Conversion into 10-Isosteroid. Chem. Pharm. Bull. 8, 46 (1960).CrossRefGoogle Scholar
  132. 132.
    Ochi, K., I. Matsunaga, M. Shindo, and C. Kaneko: Synthesis of Desmosterol and Epidesmosterol from Hyodeoxycholic Acid. Steroids 30, 2204 (1977).CrossRefGoogle Scholar
  133. 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).CrossRefGoogle Scholar
  134. 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).CrossRefGoogle Scholar
  135. 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).CrossRefGoogle Scholar
  136. 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. 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).CrossRefGoogle Scholar
  138. 138.
    Onisko, B.L., H.K. Schnoes, and H.F. Deluca: Synthesis of Potential Vitamin D Antagonists. Tetrahedron Lett. 1977, 1107.Google Scholar
  139. 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. 140.
    Palm, T.A.: The Geographical Distribution and Etiology of Rickets. Practitioner 45, 270 (1890).Google Scholar
  141. 141.
    Partridge, J.J., S. Faber, and M.R. Uskokovic: Vitamin D3 Metabolites. I. Synthesis of 25-Hydroxycholesterol. Helv. Chim. Acta 57, 764 (1974).CrossRefGoogle Scholar
  142. 143.
    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).CrossRefGoogle Scholar
  143. 144.
    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).CrossRefGoogle Scholar
  144. 145.
    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).CrossRefGoogle Scholar
  145. 146.
    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).CrossRefGoogle Scholar
  146. 147.
    Pelc, B.: 4β-Hydroxycholecalciferol and an Attempted Synthesis of its 4β-Hydroxy-epimer. J. Chem. Soc. Perkin I 1974, 1436.CrossRefGoogle Scholar
  147. 148.
    Pelc, B.: The Selenium Dioxide Oxidation of Cholecalciferol. Steroids 30, 193 (1977).CrossRefGoogle Scholar
  148. 149.
    Pelc, B., and E. Kodicek: lα-Hydroxycholesterol. J. Chem. Soc. (C) 1970, 1624.Google Scholar
  149. 150.
    Pelc, B., and D.H. Marshall: Thermal Transformation of Cholecalciferol Between 100–170°. Steroids 31, 23 (1978).CrossRefGoogle Scholar
  150. 151.
    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. 152.
    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).CrossRefGoogle Scholar
  152. 153.
    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. 154.
    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).CrossRefGoogle Scholar
  154. 155.
    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).CrossRefGoogle Scholar
  155. 156.
    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).Google Scholar
  156. 157.
    Rotman, A., and Y. Mazur: C-25 Hydroxylation of Cholesterol Derivatives. J. Chem. Soc. Chem. Comm. 1974, 15.Google Scholar
  157. 158.
    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).CrossRefGoogle Scholar
  158. 159.
    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).CrossRefGoogle Scholar
  159. 160.
    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. 161.
    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. 162.
    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).CrossRefGoogle Scholar
  162. 163.
    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).CrossRefGoogle Scholar
  163. 164.
    Salmond, W.G., and K.D. Maisto: A Synthesis of 25-Hydroxycholesterol. Tetrahedron Lett. 1977, 987.Google Scholar
  164. 165.
    Salmond, W.G., and M.C. Sobala: An Efficient Synthesis of 25-Hydroxycholesterol from Stigmasterol. Tetrahedron Lett. 1977, 1695.Google Scholar
  165. 166.
    Salmond, W.G., M.C. Sobala, and K.D. Maisto: A Synthesis of 25-Hydroxycholesterol. Tetrahedron Lett. 1977, 1237.Google Scholar
  166. 167.
    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).Google Scholar
  167. 168.
    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. 169.
    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. 170.
    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).CrossRefGoogle Scholar
  170. 171.
    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. 172.
    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).CrossRefGoogle Scholar
  172. 173.
    Sheves, M., and Y. Mazur: The Vitamin D-3,5-Cyclovitamin D Rearrangement. J. Amer. Chem. Soc. 97, 6249 (1975).CrossRefGoogle Scholar
  173. 174.
    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. 175.
    Sheves, M., and Y. Mazur: Epimerization of Vitamin D3. The Cholecalciferyl Ion. Tetrahedron Lett. 1976, 1913.Google Scholar
  175. 176.
    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. 177.
    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).CrossRefGoogle Scholar
  177. 178.
    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).CrossRefGoogle Scholar
  178. 179.
    Strating, J.: Compounds Related to Provitamin D3. IV. 3-Methylcholesterol and the Corresponding Provitamin. Rec. Trav. Chim. Pays-Bas 71, 822 (1952).CrossRefGoogle Scholar
  179. 180.
    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).CrossRefGoogle Scholar
  180. 181.
    Takeshita, T., S. Ishimoto, and N. Ikekawa: Preparation of Desmosterol from Fucosterol. Chem. Pharm. Bull. 24, 1928 (1976).CrossRefGoogle Scholar
  181. 182.
    Tanaka, Y., L. Castillo, H.F. Deluca, and N. Ikekawa: The 24-Hydroxylation of 1,25-Dihydroxyvitamin D3. J. Biol. Chem. 252, 1421 (1977).Google Scholar
  182. 183.
    Tanaka, Y., and H.F. Deluca: Biological Activity of 1,25-Dihydroxyvitamin D in the Rat. Endocrin. 92, 417 (1973).CrossRefGoogle Scholar
  183. 184.
    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).CrossRefGoogle Scholar
  184. 185.
    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).CrossRefGoogle Scholar
  185. 186.
    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. 187.
    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).CrossRefGoogle Scholar
  187. 188.
    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).CrossRefGoogle Scholar
  188. 189.
    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. 190.
    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).CrossRefGoogle Scholar
  190. 191.
    Wassermann, R.H.: Mechanism of Intestinal Calcium Absorption. Abstracts, Third Workshop on Vitamin D, California, 1976, 76.Google Scholar
  191. 192.
    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. 193.
    Wicha, J., and K. Bal: Synthesis of Preg-17(20)-en-21-oic Acid Derivatives. Syn. Comm. 7, 215 (1977).CrossRefGoogle Scholar
  193. 194.
    Windhaus, A., O. Linsert, A. Luttringhaus, and G. Weidlich: Über das kristallisierte Vitamin D2. Ann. 492, 226 (1932).Google Scholar
  194. 195.
    Windhaus, A., Fr. Schenk, and F. von Werder: Über das antirachitisch wirksame Bestrahlungsprodukt aus 7-Dehydrocholesterin. Z. Physiol. Chem. 241, 100 (1936).CrossRefGoogle Scholar
  195. 196.
    Windhaus, A., and W. Thiele: Über die Konstitution des Vitamin D2. Ann. 521, 160 (1936).Google Scholar
  196. 197.
    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).Google Scholar
  197. 198.
    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).CrossRefGoogle Scholar
  198. 199.
    Yakhimovich, R.I., N.F. Fursaeva, and G.M. Segal: Synthesis of the Fluoroanalog of Vitamin D3. Bioorg. Khim. 1976, 1526.Google Scholar
  199. 200.
    Yang, S.S., C.P. Dorn, and H. Jones: Synthesis of 25-Fluorovitamin D. Tetrahedron Lett. 1977, 2315.Google Scholar

Copyright information

© Springer-Verlag/Wien 1980

Authors and Affiliations

  • H. Jones
    • 1
  • G. H. Rasmusson
    • 1
  1. 1.Merck Institute for Therapeutic ResearchRahwayUSA

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