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Abstract

Veratrum alkaloids, like solanum and kurchi alkaloids, form a group of steroid alkaloids. The veratrum group, unlike the other two, have largely a modified steroid skeleton and exist as glyco and ester alkaloids in liliaceous plants belonging to the sub-order Melanthaceae. Although investigations on these compounds are recorded since the early nineteenth century (153), their complex structures were elucidated only during the last two decades by the independent and collaborative work of some of the world’s leading organic chemists. An added reason for recent interest in these alkaloids is the high hypotensive activity of some of their natural esters. Although this interest has waned since the discovery of the superior hypotensive ester alkaloid reserpine, extensive work on veratrum alkaloids has revealed a wealth of interesting, and at times intriguing, chemistry.

Keywords

Acetic Anhydride Secondary Hydroxyl Ether Bridge Steroid Alkaloid Lead Tetraacetate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Ahrens, F. B.: Über krystallisiertes Veratrin. Ber. dtsch. chem. Ges. 23, 2700 (1890).CrossRefGoogle Scholar
  2. 2.
    Anliker, R., H. Heusser und O. Jeger: Über Steroide und Sexualhormone. 179. Mitt. Notiz zur Herstellung von Dihydro-jervin. Helv. Chim. Acta 35, 838 (1952).CrossRefGoogle Scholar
  3. 3.
    Aslanov, KH. A. and A. S. Sadykov : Alkaloids of Fritillaria. I. Alkaloids of Fritillaria raddeana. II. Products of Chlorination of Raddeanine. III. Structure of Raddeanine. J. Gen. Chem. (USSR) 26, 579, 1790, 1794 (1956) [Chem. Abstr. 50, 13971 (1956); 51, 1993 (1957)7.Google Scholar
  4. 4.
    Augustine, R. L.: Stereochemistry of Ring F in Jervine. Chem. and Ind. 1961, 1448.Google Scholar
  5. 5.
    Auterhoff, H.: Zur Kenntnis der isomeren Formen des Veratrin-Alkamins. 2. Mitt. Arch. Pharmaz. 286, 319 (1953).CrossRefGoogle Scholar
  6. 6.
    Auterhoff, H.: Hydrierungsprodukte der Veratrin-Alkamine. 6. Mitt. Veratrin-Veratrum­Alkaloide. Arch. Pharmaz. 287, 380 (1954).CrossRefGoogle Scholar
  7. 7.
    Auterhoff, H.: Sabadilla-Nebenalkaloide. 8. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 288, 549 (1955).CrossRefGoogle Scholar
  8. 8.
    Auterhoff, H. und F. Günther: Beiträge zur Kenntnis verschiedener Veratrum-Drogen und ihrer Alkaloide. 7. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 288, 455 (1955).CrossRefGoogle Scholar
  9. 9.
    Auterhoff, H. und H. P. Kraft: Zur Kenntnis der isomeren Formen des Germins. 5. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 287, 332 (1954).CrossRefGoogle Scholar
  10. 10.
    Auterhoff, H. und H. Möhrle: Über Neosabadin - ein neues Sabadilla­Alkamin. 9. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 291, 288 (1958).CrossRefGoogle Scholar
  11. 11.
    Auterhoff, H. und H. Staúsberg: Über einige Eigenschaften des handels­üblichen Veratrins. 3. Mitt. Arch. Pharmaz. 287, 27 (1954).CrossRefGoogle Scholar
  12. 12.
    Auterhoff, H. und G. Zeisner: Über die Konstitution der Veratrin-Alkamine. 4. Mitt. Arch. Pharmaz. 286, 525 (1953).CrossRefGoogle Scholar
  13. 13.
    Bartlett, M. F., D. F. Diokel and W. I. Taylor: The Alkaloids of Tabernanthe iboga. IV. The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine. J. Amer. Chem. Soc. 80, 126 (1958).CrossRefGoogle Scholar
  14. 14.
    Barton, D. H. R.: unpublished.Google Scholar
  15. 15.
    Barton, D. H. R., C. J. W. Brooks and P. de Mayo: Steroidal Alkaloids. Part III. The Constitution and Stereochemistry of Cevine. J. Chem. Soc. (London) 1954, 3950.Google Scholar
  16. 16.
    Barton, D. H. R., C. J. W. Brooks and J. S. Fawcett: Steroidal Alkaloids. Part II. Some Observations on the Constitution of Cevine. J. Chem. Soc. (London) 1954. 2137.Google Scholar
  17. 17.
    Barton, D. H. R. and J. F. Eastham: Steroidal Alkaloids. Part I. The Functional Groups of Cevine. J. Chem. Soc. (London) 1953, 424.Google Scholar
  18. 18.
    Barton, D. H. R., O. Jeger, V. Prelog and R. B. Woodward : The Constitutions of Cevine and Some Related Alkaloids. Experientia 10, 81 (1954).CrossRefGoogle Scholar
  19. 19.
    Barton, D. H. R., F. Mccapra, P. J. May and F. Thudium: Long Range Effects in Alicyclic Systems. Part III. The Relative Rates of Condensation of Some Steroid and Triterpenoid Ketones with Benzaldehyde. J. Chem. Soc. (London) 1960, 1297; and other papers in the series.Google Scholar
  20. 20.
    Barton, D. H. R. and C. R. Narayanan: Sesquiterpenoids. Part X. The Constitution of Lactucin. J. Chem. Soc. (London) 1958, 963 (there connected references).Google Scholar
  21. 21.
    Bauer, S., L. Masler, S. Orszagh, J. Mokry and J. Tomko: Alkaloids from Fritillaria meleagris. Chem. zvesti 12 584 (1958) [Chem. Abstr. 53, 5591 (1959)].Google Scholar
  22. 22.
    Beaton, J. M., J. I. Shaw, F. S. Spring, R. Stevenson, W. S. Strachan and J. L. Stewart: Triterpenoids. Part XXXVIII. Ursa-9(11) : 13(18)-dien-­3β-yl Acetate. J. Chem. Soc. (London) 1955, 2606.Google Scholar
  23. 23.
    Bellamy, L. J.: The Infra-red Spectra of Complex Molecules. London: Methuen and Co. Ltd. 1958.Google Scholar
  24. 24.
    Blount, B. K.: The Veratrine Alkaloids. Parts I and II. The Constitution of Veratridine and Cevine. J. Chem. Soc. (London) 1935, 122.Google Scholar
  25. 25.
    Blount, B. K. and D. Crowfoot: The Veratrine Alkaloids. Part III. The Preparation of Cevanthrol and the X-Ray Crystallographic Examination of Cevanthrol and Cevanthridine. J. Chem. Soc. (London) 1936, 424.Google Scholar
  26. 26.
    Boit, H. G.: Über Imperialin. I. Mitt. Chem. Ber. 87, 472 (1954).Google Scholar
  27. 27.
    Boit, H. G. und L. Paul: Über Imperialin. II. Mitt. Chem. Ber. 90, 723 (1957).CrossRefGoogle Scholar
  28. 28.
    Bruice, T. C. and T. H. Fife: The Nature of Neighbouring Hydroxyl Group Assistance in the Alkaline Hydrolysis of the Ester Bond. Tetrahedron Letters 1961 No. 8, 263.CrossRefGoogle Scholar
  29. 29.
    Burn, D. and W. Rigby: The Skeleton of Isorubijervine. J. Chem. Soc. (London) 1953, 963.Google Scholar
  30. 30.
    Chapman, J. H., J. Elks, G. H. Phillipps and L. J. Wyman: Studies in the Synthesis of Cortisone. Part XVI. A New Method of Preparing 11-Oxo­tigogenin. J. Chem. Soc. (London) 1956, 4344.Google Scholar
  31. 31.
    Chi, Y., Y. S. Kao and K. J. Chang: The Alkaloids of Fritillaria roylei. I. Isolation of Peimine. J. Amer. Chem. Soc. 58, 1306 (1936).Google Scholar
  32. 32.
    Chou, T. Q. and T. T. Chu: The Preparation and Properties of Peimine and Peiminine. J. Amer. Chem. Soc. 63, 2936 (1941).CrossRefGoogle Scholar
  33. 33.
    Chu, T. T. and T. Q. Chou: Conversion of Peimine into Peiminine and vice versa. J. Amer. Chem. Soc. 69, 1257 (1947).CrossRefGoogle Scholar
  34. 34.
    Chu, T. T., W. K. Hwang and J. Y. Lox: Fritillaria Alkaloids. III. The Skeleton of Peimine and Peiminine by Zinc Dust Distillation and Selenium Dehydrogenation. Acta Chim Sinicia 21 232 (1955) [Chem. Abstr. 51, 444 (1957)].Google Scholar
  35. 35.
    Chu, T. T. and J. Y. Lox : Fritillaria Alkaloids. II. Peimine and Peiminine. IV. Isolation of a New Alkaloid from Si-pei-mu. Acta Chim. Sinicia 21 227, 241 (1955) [Chem. Abstr. 51, 444 (1957)].Google Scholar
  36. 36.
    Chu, T. T., J. Y. Lox and W. K. Hwang: Fritillaria Alkaloids. V. De­hydrogenation of Sipeimine and the Relationship between Sipeimine, Peimine and Peiminine. VI. The Oxidation and Reduction of Sipeimine. VII. Selenium Dehydrogenation of Sipeimine and the Relationship between Fritillaria and Veratrum Alkaloids. VIII Alkali Fusion and Acid and Alkali Treatment of Sipeimine. IX. Isolation of Several New Alkaloids from Commercial Fritillaria Species “Szechuan pei-mu”. Acta Chim. Sinicia 21 401 (1955) 22 205, 210, 356, 361 (1956) [Chem. Abstr. 51, 445 (1957)]Google Scholar
  37. 37.
    Chu, T. T., J. Y. Lox and W. K. Hwang: A Study of Fritillaria Alkaloids. X. New Alkaloids from pei-mu, a Fritillaria Species from Min Hsien. K’O Hsueh T’ung Pao No. 1, 13 (1957) [Chem. Abstr. 53, 647 (1959)1.Google Scholar
  38. 38.
    Chu, T. T., J. Y. Lox and W. K. Hwang: Fritillaria Alkaloids. XI. Proof of the Identity of Sipeimine with Imperialine. K’O Hsueh T’ung Pao 207 (1957) [Chem. Abstr. 53, 7503 (1959)].Google Scholar
  39. 39.
    Cookson, R. C. and S. H. Dandegaonker: Absorption Spectra of Ketones. Part II. The Configuration of Some Bromo-derivatives of 6-Oxocholestanyl Acetate. Absorption Spectra of a-Ketols. J. Chem. Soc. (London) 1955, 352.Google Scholar
  40. 40.
    Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. V. The Selenium Dehydrogenation of Cevine. J. Biol. Chem. 129, 79 (1939).Google Scholar
  41. 41.
    Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. VI. The Oxidation of Cevine. J. Amer. Chem. Soc. 61, 2252 (1939).CrossRefGoogle Scholar
  42. 42.
    Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. VII. On Decevinic Acid. J. Biol. Chem. 134, 123 (1940).Google Scholar
  43. 43.
    Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. VIII. Further Studies on the Selenium Dehydrogenation of Cevine. X. The Structure of Cevanthridine. J. Biol. Chem. 139, 263, 293 (1941).Google Scholar
  44. 44.
    Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. XII. Further Studies on the Oxidation of Cevine. J. Biol. Chem. 141, 253 (1941).Google Scholar
  45. 45.
    Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. XIII. The Dehydrogenation of Protoveratrine. J.Biol. Chem. 143, 427 (1942).Google Scholar
  46. 46.
    Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. XVII. On Germine. Its Formulation and Degradation. J. Biol. Chem. 148, 57 (1943).Google Scholar
  47. 47.
    Craig, L. C. and W. A. Jacobs: The Veratrine Alkaloids. XX. Further Correlations in the Veratrine Group. The Relationship between the Veratrine Bases and Solanidine. J. Biol. Chem. 149, 451 (1943).Google Scholar
  48. 48.
    Craig, L. C., W. A. Jacoss and G. I. Lavin: The Veratrine Alkaloids. IX. The Nature of the Hydrocarbon from the Dehydrogenation of Cevine. J. Biol. Chem. 139, 277 (1941).Google Scholar
  49. 49.
    Criegee, R., E. Büchner und W. Walther: Die Geschwindigkeit der Glykol­spaltung mit Blei IV-acetat in Abhängigkeit von der Konstitution des Glykols. Ber. dtsch. chem. Ges. 73, 571 (1940).CrossRefGoogle Scholar
  50. 50.
    Edwards, O. E., F. H. Clarke and B. Douglas: 17-Hydroxylupanine and 17-Oxylupanine Canad. J. Chem. 32, 235 (1954).Google Scholar
  51. 57.
    Eeles, W. T.: An X-ray Study of the Configuration of Cevine. Tetrahedron Letters 1960 No. 7, 24.CrossRefGoogle Scholar
  52. 52.
    Elming, N., C. Vogel, O. Jeger und V. Prelog: Veratrum-Alkaloide. 2. Mitt. Über die Konstitution der Hexan-tetracarbonsäure aus Cevin und Germin. Helv. Chim. Acta 35, 2541 (1952).CrossRefGoogle Scholar
  53. 53.
    Elming, N., C. Vogel, O. Jeger und V. Prelog: Veratrum-Alkaloide. 3. Mitt. Zur Konstitution der Hexan­tetracarbonsäure aus Cevin und Germin. II. Helv. Chim. Acta 36, 2022 (1953).CrossRefGoogle Scholar
  54. 53a.
    Erskine, R. L. and E. S. Waight: Stereochemistry and Infrared Spectra of a,ß-Unsaturated Ketones. J. Chem. Soc. (London) 1960, 3425.Google Scholar
  55. 54.
    Fieser, L. F. and M. Fieser: Steroids. New York: Reinhold Publ. Corp. 1959.Google Scholar
  56. 55.
    Fragner, K.: Ein neues Alkaloid Imperialin. Ber. dtsch. chem. Ges. 21, 3284 (1888).CrossRefGoogle Scholar
  57. 56.
    Freund, M. : Beitrag zur Kenntnis des Cevadins. Ber. dtsch. them. Ges. 37, 1946 (1904).CrossRefGoogle Scholar
  58. 57.
    Freund, M. und H. P. Schwarz: Beitrag zur Kenntnis des Cevadins. Ber. dtsch. chem. Ges. 32, 800 (1899).CrossRefGoogle Scholar
  59. 58.
    Freund, M. und A. Schwarz: Cevadin. III. J. prakt. Chem. 96, 237 (1918).Google Scholar
  60. 59.
    Fried, J. and A. Klingsberg: The Structure of Jervine. III. Degradation to Nitrogen Free Derivatives. J. Amer. Chem. Soc. 75, 4929 (1953).CrossRefGoogle Scholar
  61. 60.
    Fried, J., P. Numerof and N. H. Coy: Neogermitrine, A New Ester Alkaloid from Veratrum viride. J. Amer. Chem. Soc. 74, 3045 (1952).Google Scholar
  62. 61.
    Fried, J., H. L. White and O. Wintersteiner: The Hypotensive Principles of Veratrum viride. J. Amer. Chem. Soc. 72, 4621 (1950).CrossRefGoogle Scholar
  63. 62.
    Fried, J., O. Wintersteiner, M. Moore, B. M. Iselin and A. Klingsberg: The Structure of Jervine. II. Degradation to Perhydrobenzfluorene Derivatives. J. Amer. Chem. Soc. 73, 2970 (1951).CrossRefGoogle Scholar
  64. 63.
    Gautschi, F., O. Jeger, V. Prelog und R. B. Woodward: Veratrum-Alkaloide. 5. Mitt. Über die Konstitution der Decevinsäure. Heiv. Chim. Acta 37, 2280 (1954).CrossRefGoogle Scholar
  65. 64.
    Gautschi, F., O. Jeger, V. Prelog und R. B. Woodward: Veratrum-Alkaloide. 9. Mitt. Absolute Konfiguration des Kohlenstoffatoms ro in Cevin und verwandten Alkaloiden. Heiv. Chim. Acta 38, 296 (1955).CrossRefGoogle Scholar
  66. 65.
    Gillam, A. E. and E. S. Stern: An Introduction to Electronic Absorption Spectroscopy in Organic Chemistry. London: E. Arnold, Ltd. 1957.Google Scholar
  67. 66.
    Goodman, L. S. and A. Gilman: The Pharmacological Basis of Therapeutics, 2nd ed., pp. 747–754. New York: Macmillan Co. 1955.Google Scholar
  68. 67.
    Henbest, H. B. and B. J. Lovell: Aspects of Stereochemistry. Part II. Intramolecular Electrophilic Assistance in Displacement Reactions. J. Chem. Soc. (London) 1957, 1965.Google Scholar
  69. 68.
    Hennig, A. J., T. Higuchi and L. M. Parks: Sabadilla Alkaloids. III. Chromatographic Separation of the Water Soluble Fraction. Isolation of a New Crystalline Alkaloid Sabatine. J. Amer. Pharmaceut. Assoc. 40, 168 (1951).CrossRefGoogle Scholar
  70. 69.
    Herz, J. E. and J. Fried: Jervine. VII. 3,5-Cyclo Derivatives of Jervine Degradation Products. J. Amer. Chem. Soc. 76, 5621 (1954).CrossRefGoogle Scholar
  71. 70.
    Hess, K. und H. Mohr: Über das Cevin und Sabadinin. Ber. dtsch. chem. Ges. 52, 1984 (1919).CrossRefGoogle Scholar
  72. 71.
    Heyl, F. W., F. E. Hepner and S. K. Loy: Zygadenine. The Crystalline Alkaloid of Zygadenus intermedius. J. Amer. Chem. Soc. 35, 258 (1913).CrossRefGoogle Scholar
  73. 72.
    Heyl, F. W. and M. E. Herr: The Formula of Zygadenine. J. Amer. Chem. Soc. 71, 1751 (1949).CrossRefGoogle Scholar
  74. 73.
    Heymann, H. and L. F. Fieser: A New Route to II-Ketosteroids by Fission of a 49(11)-Ethylene Oxide. J. Amer. Chem. Soc. 73, 5252 (1951).CrossRefGoogle Scholar
  75. 74.
    Hirschmann, R., C. S. Snoddy, Jr., C. F. Hiskey and N. L. Wendler: The Rearrangement of the Steroid CID Rings. J. Amer. Chem. Soc. 76, 4013 (1954).CrossRefGoogle Scholar
  76. 75.
    Hosansky, N. L. and O. Wintersteiner: 8,9-Seto Derivatives of Triacetyl Dihydro Veratramine. J. Amer. Chem. Soc. 78, 3126 (1956).CrossRefGoogle Scholar
  77. 76.
    Huebner, C. F. and W. A. Jacobs: The Veratrine Alkaloids. XXVI. On the Hexanetetracarboxylic Acid from Cevine and Germine. J. Biol. Chem. 170, 181 (1947).Google Scholar
  78. 77.
    Iselin, B. M., M. Moore and O. Jervine, IX. Miscellaneous New Derivatives. J. Amer. Chem. Soc. 78, 403 (1956).CrossRefGoogle Scholar
  79. 78.
    Iselin, B. M. and O. Wintersteiner: Jervine. VI. The Sulfuric Acid-catalyzed Acetolysis of N-Acetyl-3-desoxy-3(a)-chlorotetrahydrojervine. J. Amer. Chem. Soc. 76, 5616 (1854).CrossRefGoogle Scholar
  80. 79.
    Iselin, B. M. and O. Wintersteiner: Jervine. VIII. z113-Jervine, a New Double Bond Isomer of Jervine. J. Amer. Chem. Soc. 77, 5318 (1955).CrossRefGoogle Scholar
  81. 80.
    Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. I. The Degradation of Cevine. II. Further Study of the Basic Degradation Products of Cevine. III. Further Studies on the Degradation of Cevine, the Question of Coniine. IV. The Degradation of Cevine Methiodide. J. Biol. Chem. 119, 141 (1937) 120, 447 (1937); 124, 659 (1938); 125, 625 (1938).Google Scholar
  82. 81.
    Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XV. On Rubijervine and Isorubijervine. J. Biol. Chem. 148, 41 (1943).Google Scholar
  83. 82.
    Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XVI. The Formulation of Jervine. J. Biol. Chem. 148, 51 (1943).Google Scholar
  84. 83.
    Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XIX. On Protoveratrine and its Alkamine Protoverine. J. Biol. Chem. 149, 271 (1943).Google Scholar
  85. 84.
    Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XXI. The Conversion of Rubijervine to Allorubijervine. The Sterol Ring System of Rubijervine. J. Biol. Chem. 152, 641 (1944).Google Scholar
  86. 85.
    Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XXII. On Pseudojervine and Veratrosine, a Companion Glycoside in Veratrum viride. J. Biol. Chem. 155, 565 (1944).Google Scholar
  87. 86.
    Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XXIII. The Ring System of Rubijervine and Isorubijervine. J. Biol. Chem. 159, 617 (1945).Google Scholar
  88. 87.
    Jacobs, W. A. and L. C. Craig: The Veratrine Alkaloids. XXV. The Alkaloids of Veratrum wide. J. Biol. Chem. 160, 555 (1945).Google Scholar
  89. 88.
    Jacobs, W. A., L. C. Craig and G. I. Lavin: The Veratrine Alkaloids. XI. The Dehydrogenation of Jervine. J. Biol. Chem. 141, 51 (1941).Google Scholar
  90. 89.
    Jacobs, W. A. and C. F. Huebner: The Veratrine Alkaloids. XXVII. Further Studies with Jervine. J. Biol. Chem. 170, 635 (1947).Google Scholar
  91. 90.
    Jacoss, W. A. and S. W. Pelletier: The Veratrine Alkaloids. XXXVI. A Possible Skeletal Structure for Veracevine, Cevine, Germine and Protoverine. J. Organ. Chem. (USA) 18, 765 (1953).Google Scholar
  92. 91.
    Jacobs, W. A. and Y. Sato: The Veratrine Alkaloids. XXVIII. The Structure of Jervine. J. Biol. Chem. 175, 57 (1948).Google Scholar
  93. 92.
    Jacobs, W. A. and Y. Sato: The Veratrine Alkaloids. XXX. A Further Study of the Structure of Veratramine and Jervine. J. Biol. Chem. 181, 55 (1949).Google Scholar
  94. 93.
    Jacobs, W. A. and Y. Sato: The Veratrine Alkaloids. XXXII. The Structure of Veratramine. J. Biol. Chem. 191, 71 (1951).Google Scholar
  95. 94.
    Jaffe, H. and W. A. Jacoss: The Veratrine Alkaloids. XXXIII. The Isomeric Forms of Cevine, Germine and Protoverine. J. Biol. Chem. 193, 325 (1951).Google Scholar
  96. 95.
    Jeger, O., R. Mirza, V. Prelog, C. Vogel und R. B. Woodward: Veratrum­Alkaloide. 6. Mitt. Die Konstitution der Hexan-tetracarbonsäure aus Cevin und Germin. Rely. Chim. Acta 37, 2295 (1954).CrossRefGoogle Scholar
  97. 96.
    Jeger, O. and V. Prelog: Steroid Alkaloids. Veratrum Group. In: R. H. F. Manske, The Alkaloids, Chemistry and Physiology, Vol. 7, P. 363. New York: Academic Press. 1960.Google Scholar
  98. 97.
    Jeger, O., V. Prelog, E. Sundt und R. B. Woodward: Veratrum-Alkaloide. 7. Mitt. Die Konstitution des Ringes F und die absolute Konfiguration des Kohlenstoffatoms 25 des Cevins. Rely. Chim. Acta 37, 2302 (1954).CrossRefGoogle Scholar
  99. 98.
    Keller, L., CH. Tamm und T. Reichstein: Synthese des 7-Athyl-I,2-benzo­fluorens und des 7-Äthyl-8-methyl-I,2-benzofluorens und Identifizierung des letzteren mit dem Jacobs’schen Kohlenwasserstoff. Glykoside und Aglykone, 192. Mitt. Hely. Chim. Acta 41 1633 (1958).CrossRefGoogle Scholar
  100. 99.
    Kerstan, W. : Veratrum Alkaloide. Pharm. Zentralhalle 96, 251 (1957).Google Scholar
  101. 100.
    Kimishjma, K. and T. Kanno: Certain Pharmacological Actions of Veratramine. Yonago Igku Zasshi 8, 429 (1957) [Chem. Abstr. 53, 573 (1959)].Google Scholar
  102. 201.
    Klohs, M. W., R. Arons, M. D. Draper, F. Keller, S. Koster, W. Malesh and F. J. Petracek : The Isolation of Neoprotoveratrine and Protoveratrine from Veratrum viride AIT. J. Amer. Chem. Soc. 74, 5107 (1952).CrossRefGoogle Scholar
  103. 102.
    Klohs, M. W., M. D. Draper, F. Keller, S. Koster, W. Malesh and F. J. Petracek: The Alkaloids of Veratrum fimbriatum GRAY. J. Amer. Chem. Soc. 75, 4925 (1953).CrossRefGoogle Scholar
  104. 103.
    Klohs, M. W., M. D. Draper, F. Keller, S. Koster, W. Malesh and F. J. Petracek: Alkaloids of Veratrum eschscholtzii GRAY. II. The Ester Alkaloids. J. Amer. Chem. Soc. 76, 1152 (1954).CrossRefGoogle Scholar
  105. 104.
    Klohs, M. W., M. D. Draper, F. Keller, W. Malesh and F. J. Petracek: Alkaloids of Veratrum eschscholtzii GRAY. I. The Glycosides. J. Amer. Chem. Soc. 75, 2133 (1953).CrossRefGoogle Scholar
  106. 105.
    Klohs, M. W., M. D. Draper, F. Keller, W. Malesh and F. J. Petracek: The Isolation of Desacetylneoprotoveratrine from Veratrum viride AIT. J. Amer. Chem. Soc. 75, 3595 (1953).CrossRefGoogle Scholar
  107. 106.
    Krayer, O.: Veratrum Alkaloids. In: V. A. DRILL, Pharmacology in Medicine, 2nd ed., pp. 515–524. New York: McGraw Hill Book Co. 1958.Google Scholar
  108. 107.
    Kupchan, S. M.: Hypotensive Veratrum Ester Alkaloids. J. Pharmaceut. Sci. (USA) 50, 273 (1961).CrossRefGoogle Scholar
  109. 108.
    Kupchan, S. M.: Schoenocaulon Alkaloids. IV. The Isomeric Cevagenine Orthoacetates. J. Amer. Chem. Soc. 77, 686 (1955).CrossRefGoogle Scholar
  110. 109.
    Kupchan, S. M.: Veratrum Alkaloids. XXIX. The Structures of Germitrine, Neogermitrine and Several Related Hypotensive Ester Alkaloids. J. Amer. Chem. Soc. 81, 1921 (1959).CrossRefGoogle Scholar
  111. 110.
    Kupchan, S. M.: Veratrum Alkaloids. XXX. The Structure and Configuration of Zygadenine. J. Amer. Chem. Soc. 81, 1935 (1959).CrossRefGoogle Scholar
  112. 111.
    Kupchan, S. M. and A. Afonso: Veratrum Alkaloids. XXXVII. The Structure of Germanitrine, a Hypotensive Ester Alkaloid. J. Amer. Pharmaceut. Assoc. 48, 731 (1959).CrossRefGoogle Scholar
  113. 112.
    Kupchan, S. M. and A. Afonso: Veratrum Alkaloids. XLIII. The Structure of Cevadine. J. Amer. Pharmaceut. Assoc. 49, 242 (1960).CrossRefGoogle Scholar
  114. 113.
    Kupchan, S. M. and C. I. Ayres: Veratrum Alkaloids. XXXII. The Structures of Germitetrine and Some Related Hypotensive Ester Alkaloids. J. Amer. Pharmaceut. Assoc. 48, 440 (1959).CrossRefGoogle Scholar
  115. 114.
    Kupchan, S. M. and C. I. Ayres: Veratrum Alkaloids. XXXIX. The Structures of Protoveratrine A and Protoveratrine B. J. Amer. Chem. Soc. 82 2252 (1960).CrossRefGoogle Scholar
  116. 115.
    Kupchan, S. M. and C. I. Ayres: Veratrum Alkaloids. XL. The Structure of Escholerine, a Hypotensive Ester Alkaloid. J. Amer. Pharnaceut. Assoc. 48, 735 (1959).CrossRefGoogle Scholar
  117. 115a.
    Kupchan, S. M., C. I. Ayres and R. H. Hensler: Veratrum Alkaloids. XLII. The Structures of Desacetylprotoveratrine A and Desacetylproto­veratrine B. J. Amer. Chem. Soc. 82, 2616 (1960).CrossRefGoogle Scholar
  118. 116.
    Kupchan, S. M., C. I. Ayres, M. Neeman, R. H. Hensler, T. Masamune and S. Rajagopalan: Veratrum Alkaloids. XXXVIII. The Structure and Configuration of Protoverine. J. Amer. Chem. Soc. 82 2242 (1960).CrossRefGoogle Scholar
  119. 117.
    Kupchan, S. M. and C. V. Deliwala: Zygadenus Alkaloids. III. Active Principles of Zygadenus venenosus. Veratroylzygadenine and Vanilloylzygadenine. IV. Germine Esters. J. Amer. Chem. Soc. 75, 1025 (1953); 76, 5545 (1954).Google Scholar
  120. 118.
    Kupchan, S. M. and C. V. Deliwala: The Isolation of Crystalline Hypotensive Veratrum Ester Alkaloids by Chromatography. J. Amer. Chem. Soc. 75, 4671 (1953).CrossRefGoogle Scholar
  121. 119.
    Kupchan, S. M., C. V. Deliwala and R. D. Zoxls: Zygadenus Alkaloids. VI. Active Principles of Zygadenus paniculatus. J. Amer. Chem. Soc. 77, 755 (1955).CrossRefGoogle Scholar
  122. 120.
    Kupchan, S. M., M. Fieser, C. R. Narayanan, L. F. Fieser and J. Fried: The Germine-Isogermine-Pseudogermine Isomerizations. J. Amer. Chem. Soc. 77, 5896 (1955).CrossRefGoogle Scholar
  123. 121.
    Kupchan, S. M., J. C. Grivas, C. I. Ayres, L. J. Pandya and L. C. Weaver: Veratrum Alkaloids. XLVI. Structure Activity Relationship in a Series of Analogs of the Protoveratrines. J. Pharmaceut. Sci. (USA) 50, 396 (1961).CrossRefGoogle Scholar
  124. 122.
    Kupchan, S. M. and N. Gruenfeld: Veratrum Alkaloids. XLI. The Structure of Germbudine, A Hypotensive Ester Alkaloid. J. Amer. Pharmaceut. Assoc. 48, 737 (1959).CrossRefGoogle Scholar
  125. 123.
    Kupchan, S. M., R. H. Hensler and L. C. Weaver: Veratrum Alkaloids. XLIV. Structure Activity Relationships in a Series of Synthetic Hypotensive Esters of Protoverine. J. Med. Pharmaceut. Chem. (USA) 3, 129 (1961).CrossRefGoogle Scholar
  126. 124.
    Kupchan, S. M., W. S. Johnson and S. Rajagopalan: The Configuration of Cevine. Tetrahedron 7, 47 (1959).CrossRefGoogle Scholar
  127. 125.
    Kupchan, S. M. and D. Lavie: Schoenocaulon Alkaloids. III. The Bismuth Oxide Oxidation of Veracevine, Cevagenine and Cevine. J. Amer. Chem. Soc. 77, 683 (1955).CrossRefGoogle Scholar
  128. 126.
    Kupchan, S. M., D. Lavie, C. V. Deliwala and B. Y. A. Andoh: Schoenocaulon Alkaloids. I. Active Principles of Schoenocaulon officinale. Cevacine and Protocevine. J. Amer. Chem. Soc. 75, 5519 (1953).CrossRefGoogle Scholar
  129. 127.
    Kupchan, S. M., D. Lavie and R. D. Zonis: Zygadenus Alkaloids. V. Active Principles of Zygadenus venenosus. Zygacine. J. Amer. Chem. Soc. 77, 689 (1955).CrossRefGoogle Scholar
  130. 128.
    Kupchan, S. M. and T. Masamune: Structure of the Presumed Hofmann Elimination Product of Cevine Methiodide. Chem. and Ind. 1959, 632.Google Scholar
  131. 129.
    Kupchan, S. M. and C. R. Narayanan: The Structure of Germine and Some Related Hypotensive Ester Alkaloids. Chem. and Ind. 1956, 1093.Google Scholar
  132. 130.
    Kupchan, S. M. and C. R. Narayanan: Veratrum Alkaloids. XVIII. The Structure and Configuration of Germine. J. Amer. Chem. Soc. 81, 1913 (1959).CrossRefGoogle Scholar
  133. 131.
    Kupchan, S. M., P. Slade and R. J. Young: Intramolecular Catalysis. Facilitation of Alkaline Hydrolysis of Alicyclic 1,2-Diol Monoesters. Tetra­hedron Letters 1960 No. 24, 22.CrossRefGoogle Scholar
  134. 132.
    Kupchan, S. M., L. C. Weaver, C. I. Ayres and R. H. Hensler: Veratrum Alkaloids. XLV. Structure Activity Relationship in a Series of Protoverine Derivatives. J. Pharmaceut. Sci. (USA) 50, 52 (1961).CrossRefGoogle Scholar
  135. 133.
    Leonard, N. J. and M. A. Rebenstorf: Lead Tetraacetate Oxidation of Amino Alcohols. J. Amer. Chem. Soc. 67, 49 (1945).CrossRefGoogle Scholar
  136. 134.
    Macbeth, A. K. and R. Robinson: Cevadine. Part I. J. Chem. Soc. (London) 121 1571 (1922).Google Scholar
  137. 135.
    Macek, K., S. Vanécek, V. Pelcovil und Z. J. Vejdélek: Veratrum-Alkaloide. IV. Analyse des Veratrins mit Hilfe der Papierchromatographie. Collect. Czech. Chem. Commun. 21, 1182 (1956).Google Scholar
  138. 136.
    Macek, K., S. Vanmek und Z. J. Vejdélek: Veratrum-Alkaloide. II. Über die Papierchromatographie der Alkaloide aus Schoenocaulon officinale und einiger Strukturanaloga. Collect. Czech. Chem. Commun. 21, 987 (1956).Google Scholar
  139. 137.
    Macek, K., S. Vanmek und Z. J. Vejdélek: Veratrum-Alkaloide. VI. Beitrag der Papierchromatographie zur Lösung von Strukturfragen. Collect. Czech. Chem. Commun. 22, 253 (1957).Google Scholar
  140. 138.
    Maison, G. L., E. Gotz and J. W. Stutzman: Relative Hypotensive Activity of Certain Veratrum Alkaloids. J. Pharmacol. exp. Therapeut. 103, 74 (1951).Google Scholar
  141. 139.
    Mckenna, J.: Steroidal Alkaloids. Quart. Rev. (Chem. Soc. London) 7, 231 (1953).CrossRefGoogle Scholar
  142. 140.
    Mijovié, M. V., E. Sundt, E. Kyburz, O. Jeger und V. Prelog: Veratrum­Alkaloide. 8. Mitt. Über die Konstitution der Ringe C und D des Cevadins und verwandter Alkaloide. Rely. Chim. Acta 38, 231 (1955).CrossRefGoogle Scholar
  143. 141.
    Mitchner, H. and L. M. Parks: Sabadilla Alkaloids. VI. Separation of Veratridine and Cevadine by Countercurrent Distribution; pH vs. Partition Coefficients. J. Amer. Pharmaceut. Assoc., Sci. Ed. 45, 549 (1956).CrossRefGoogle Scholar
  144. 142.
    Mitchner, H. and L. M. Parks: Sabadilla Alkaloids. VII. Sabatine and its Alkamine Sabine. J. Amer. Pharmaceut. Assoc. 48, 303 (1959).CrossRefGoogle Scholar
  145. 142a.
    Mitsuhashi, H. and Y. Shimizu: Synthesis of a Nitrogen-free Derivative of Jervine. Tetrahedron Letters 1961, No. 21, 777.CrossRefGoogle Scholar
  146. 143.
    Möhrle, H. und H. Auterhoff: Die Konstitution des Sabadins. to. Mitt. Veratrin-Veratrum-Alkaloide. Arch. Pharmaz. 292 337 (1959).CrossRefGoogle Scholar
  147. 144.
    Möhrle, H. und H. Auterhoff: Zur Kenntnis der Reaktion von Sabadilla-Alkaminen mit Perjodat. LI. Mitt. Sabadilla-und Veratrum-Alkaloide. Arch. Pharmaz. 293 813 (1960).CrossRefGoogle Scholar
  148. 145.
    Morgan, K. J.: Thesis, Oxford Univ. (1952) [cf. Ref. 146].Google Scholar
  149. 146.
    Morgan, K. J. and J. A. Barltrop: Veratrum Alkaloids. Quart. Rev. (Chem. Soc. London) 12 34 (1958).CrossRefGoogle Scholar
  150. 147.
    Myers, G. S., W. L. Glen, P. Morozovitch, R. Barber, G. Papineau-Couture and G. A. Grant: Some Hypotensive Alkaloids from Veratrum album. J. Amer. Chem. Soc. 78, 1621 (1956).CrossRefGoogle Scholar
  151. 148.
    Myers, G. S., P. Morozovitch, W. L. Glen, R. Barber, G. Papineau-Couture and G. A. Grant: Some New Hypotensive Ester Alkaloids from Veratrum viride. J. Amer. Chem. Soc. 77, 3348 (1955).CrossRefGoogle Scholar
  152. 149.
    Nash, H. A. and R. M. Brooker: Hypotensive Alkaloids from Veratrum album. Protoveratrine A, Protoveratrine B and Germitetrine B. J. Amer. Chem. Soc. 75, 1942 (1953).CrossRefGoogle Scholar
  153. 150.
    Neuss, N.: A New Alkaloid from Amianthium Muscaetoxicum GRAY. J. Amer. Chem. Soc. 75, 2772 (1953).CrossRefGoogle Scholar
  154. 151.
    Okuda, S., K. Tsuda and H. Kataoka: Absolute Configuration at C(25) in Jervine and Veratramine. Chem. and Ind. 1961, 512.Google Scholar
  155. 152.
    Paul, L. und H. G. Boit: Nebenalkaloide von Fritillaria imperialis. III. Mitt. über Fritillaria-Alkaloide. Chem. Ber. 91, 1968 (1958).CrossRefGoogle Scholar
  156. 153.
    Pelletier, P. J., J. B. Caventou: Examen chimique de plusieurs végétaux de la famille des colchicées, et du principe actif qu’ils renferment [Cévadille (veratrum sabadilla) ; hellébore blanc (veratrum album) ; colchique commun (colchicum autumnale)]. Ann. Chim. [2], 14, 69 (1820).Google Scholar
  157. 154.
    Pelletier, S. W. and W. A. Jacobs: The Veratrine Alkaloids. XXXV. Vera­cevine, the Alkanolamine of Cevadine and Veratridine. J. Amer. Chem. Soc. 75, 3248 (1953).CrossRefGoogle Scholar
  158. 155.
    Pelletier, S. W. and W. A. Jacobs: The Veratrine Alkaloids. XXXVII. The Structure of Isorubijervine. Conversion to Solanidine. J. Amer. Chem. Soc. 75, 4442 (1953).CrossRefGoogle Scholar
  159. 156.
    Pelletier, S. W. and W. A. Jacobs: The Veratrine Alkaloids. XXXIX. A Study of Certain Selenium Dehydrogenation Products of Cevine. J. Amer. Chem. Soc. 78, 1914 (1956).CrossRefGoogle Scholar
  160. 157.
    Pelletier, S. W. and D. M. Locxe: The Veratrum Alkaloids. XLI. The Position of the Second Hydroxyl in Rubijervine and the Identity of Certain Dehydrogenation Products. J. Amer. Chem. Soc. 79, 4531 (1957).CrossRefGoogle Scholar
  161. 158.
    Poethee, W.: Die Alkaloide von Veratrum album. 1. Mitt.: Darstellung der Alkaloide und ihre Verteilung in Rhizomen, Wurzeln und Blattbasen. — Germerin, ein neues Alkaloid von Vevatrum album. — z. Mitt.: Die einzelnen Alkaloide und ihre Beziehungen zueinander. Protoveratridin, Germerin, Protoveratrin. Arch. Pharmaz. 275, 357, 571 (1937).CrossRefGoogle Scholar
  162. 159.
    Poethke, W. : Die Alkaloide von Veratrum album. 3. Mitt. : Jervin, Pseudo­jervin, Rubijervin. Einteilung der Alkaloide. Arch. Pharmaz. 276, 170 (1938).CrossRefGoogle Scholar
  163. 160.
    Preininger, V. and F. Santavÿ: Polarography of Alkaloids. XXII. A Polarographic Study of Veratrum Alkaloids. Collect. Czech. Chem. Commun. 23, 1153 (1958).Google Scholar
  164. 161.
    Prelog, V. and O. Jeger: The Chemistry of Veratrum Alkaloids. In: R. H. F. Manske and H. L. Holmes, The Alkaloids, Chemistry and Physiology, Vol. 3, p. 243. New York: Academic Press Inc. 1953.Google Scholar
  165. 162.
    Rosenfelder, W. J.: The Methanolysis of Some Acetyl Derivatives of Cevine. J. Chem. Soc. (London) 1954, 2638.Google Scholar
  166. 163.
    Saito, K.: Veratramine, a New Alkaloid of White Hellebore (Veratrum grandiflorum LoES fil.). Bull. Chem. Soc. Japan 15, 22 (1940).CrossRefGoogle Scholar
  167. 164.
    Saito, K., H. Suginome and M. Takaoka: The Alkaloids of White Hellebore. t. Isolation of Constituent Alkaloids. Bull. Chem. Soc. Japan 9, 15 (1934).CrossRefGoogle Scholar
  168. 165.
    Salzberger, G.: Über die Alkaloide der weißen Nieswurz (Veratrum album). Arch. Pharmaz. 228, 462 (1890).CrossRefGoogle Scholar
  169. 166.
    Sato, Y. and W. A. Jacoss: The Veratrine Alkaloids. XXIX. The Structure of Rubijervine. J. Biol. Chem. 179, 623 (1949).Google Scholar
  170. 167.
    Sato, Y. and W. A. Jacoss: The Veratrine Alkaloids. XXXI. The Structure of Isorubijervine. J. Biol. Chem. 191, 63 (1951).Google Scholar
  171. 168.
    Shaligram, A. M.: Studies in Essential Oils. Ph. D. Thesis, Poona Univ., 1961. — A. M. SHALIGRAM, A. S. RAO and S. C. BHATTACHARYYA: Absolute Configuration of Junenol and Laevojunenol and Synthesis of Junenol from Costunolide. Tetrahedron (in press) (1962).Google Scholar
  172. 168a.
    Sheehan, J. C., R. L. Young and P. A. Cruickshank: C16-C18 Rearrangements of Steroid Alkaloids. J. Amer. Chem. Soc. 82, 6147 (1960).CrossRefGoogle Scholar
  173. 169.
    Sicher, J. and M. Tichy: The Relative Configuration at C22 and C23 in Veratramine and Jervine. Tetrahedron Letters 1959, No. 12, 6.CrossRefGoogle Scholar
  174. 170.
    Stoll, A.: Les alcaloïdes du Vératrum. Gazz. chim. ital. 84, 1190 (1954).Google Scholar
  175. 171.
    Stoll, A. und E. Seebeck: Die Spaltprodukte von Cevadin und Veratridin bei alkalischer Hydrolyse. 2. Mitt. über Veratrum-Alkaloide. Hely. Chim. Acta 35, 1270 (1952).CrossRefGoogle Scholar
  176. 172.
    Stoll, A. und E. Seebeck: Derivate des Cevadins und des Cevagenins und über die Eigenschaften und die vermutliche Lage der Sauerstoffatome im Cevagenin. 4. Mitt über Veratrum-Alkaloide. Heiv. Chim. Acta 35, 1942 (1952).CrossRefGoogle Scholar
  177. 173.
    Stoll, A. und E. Seebeck: Über zwei Isomere des a-Cevins. 5. Mitt. über Veratrum-Alkaloide. Rely. Chim. Acta 36, 189 (1953).CrossRefGoogle Scholar
  178. 174.
    Stoll, A. und E. Seebeck: Über Protoveratrin A und Protoveratrin B. 6. Mitt. über Veratrum­Alkaloide. Rely. Chim Acta 36, 718 (1953).CrossRefGoogle Scholar
  179. 175.
    Stoll, A. und E. Seebeck: Veratroyl-zygadenin aus Veratrum album. 7. Mitt. über Veratrum­Alkaloide. Hely. Chim. Acta 36, 1570 (1953).CrossRefGoogle Scholar
  180. 176.
    Stoll, A. und E. Seebeck: Über eine Orthoessigsäureester-Gruppierung in den Acetylierungs­produkten von Cevadin und Cevagenin. 9. Mitt. über Veratrum-Alkaloide. Hely. Chim. Acta 37, 824 (1954).CrossRefGoogle Scholar
  181. 177.
    Stoll, A. und E. Seebeck: Veratrobasine and Geralbine, two New Alkaloids Isolated from Veratrum album. J. Amer. Chem. Soc. 74, 4728 (1952).CrossRefGoogle Scholar
  182. 178.
    Stoll, A., D. Stauffacher und E. Seebeck: Nachweis einer a-Ketol-Gruppie­rung im Cevagenin. 8. Mitt. über Veratrum-Alkaloide. Hely. Chim. Acta 36, 2027 (1953).CrossRefGoogle Scholar
  183. 179.
    Stoll, A., D. Stauffacher und E. Seebeck: Über Veratrobasin. 10. Mitt. über Veratrum-Alkaloide. Helv. Chim. Acta 38, 1964 (1955).CrossRefGoogle Scholar
  184. 180.
    Stuart, D. M. and L. M. Parks : Sabadilla Alkaloids. V. Vanilloylcevine. J. Amer. Pharmaceut. Assoc. 45, 252 (1956).CrossRefGoogle Scholar
  185. 181.
    Sundt, E., O. Jeger and V. Prelog: Conversion of Cevagenin into a Diosphenol. Chem. and Ind. 1953, 1365.Google Scholar
  186. 182.
    Suzuki, M., Y. Murase, R. Hayashi and N. Sandei: Constituent of Veratrum album. J. pharmac. Soc. Japan 79, 619 (1959) [Chem. Abstr. 53, 22050 (1959)].Google Scholar
  187. 183.
    Swiss, E. D.: Emetic Properties of Veratrum Derivatives. J. Pharmacol. exp. Therapeut. 104, 76 (1952).Google Scholar
  188. 184.
    Swiss, E. D. and G. L. Maison: New Alkaloids of Veratrum. Federat. Proc. (Amer. Soc. exp. Biol.) 11, 395 (1952).Google Scholar
  189. 185.
    Tamm, CH. and O. Wintersteiner: The Structure of Veratramine. J. Amer. Chem. Soc. 74, 3842 (1952).CrossRefGoogle Scholar
  190. 186.
    Uffer, A.: Holarrhenin aus Holarrhena congolensis STAPF. Helv. Chim Acta 39, 1834 (1956).CrossRefGoogle Scholar
  191. 187.
    Uhle, F. and W. A. Jacobs: The Veratrine Alkaloids. XXIV. The Octa­hydropyrrocoline Ring System of the Tertiary Bases. Conversion of Sara­sapogenin to a Solanidine Derivative. J. Biol. Chem. 160, 243 (1945).Google Scholar
  192. 188.
    Uhle, F. C., J. E. Krueger and F. Sallmann: N-Alkyl Derivatives of Veratramine. J. Amer. Chem. Soc. 82, 489 (1960).CrossRefGoogle Scholar
  193. 189.
    Vansheidt, A. A.: Fluorene and Triphenylmethane Hydrocarbons. XIII. Alcoholic Alkali as a Reagent for Fluorene Hydrocarbons with a Mobile Hydrogen. J. Gen. Chem. (USSR) 4, 875 (1934) [Chem. Abstr. 29, 2160 (1935)].Google Scholar
  194. 190.
    Vejdělek, Z. J., K. Macek und B. Buděšínský: Veratrum-Alkaloide. V. Über Synthese und Struktur einiger neuer Ester des Veracevins, Cevagenins und Cevins. Partialsynthese des Cevacins und Veratridins. Collect. Czech. Chem. Commun. 22, 98 (1957).Google Scholar
  195. 191.
    Vejdělek, Z. J., K. Macek und B. Kakáč: Veratrum-Alkaloide. III. Über die Inhaltsstoffe des Veratrins. Collect. Czech. Chem. Commun. 21 995 (1956).Google Scholar
  196. 192.
    >Vejdělek, Z. J., K. Macek und V. Trčka: Veratrum-Alkaloide. VII. Ge­mischte Veracevinester. Collect. Czech. Chem. Commun. 22 816 (1957).Google Scholar
  197. 193.
    Vejdělek, Z. J. und V. Trčka: Veratrum-Alkaloide. I. Über einige Ester des Cevins und die Zusammensetzung des „Cevindikaliums“. Collect. Czech. Chem. Commun. 21 743 (1956).Google Scholar
  198. 194.
    Weisenborn, F. L. and J. W. Bolger: The Synthesis of Monoacetylneo­germitrine and Germidine from Germine. J. Amer. Chem. Soc. 76, 5543 (1954).CrossRefGoogle Scholar
  199. 195.
    Weisenborn, F. L., J. W. Bolger, D. B. Rosen, L. T. Mann, Jr., L. Johnson and H. L. Holmes: Synthetic Hypotensive Esters from Germine. J. Amer. Chem. Soc. 76, 1792 (1954).CrossRefGoogle Scholar
  200. 196.
    Wfisenborn, F. L. and D. Burn : The Structure of Isorubijervine. — Conversion to Solanidine and Solanidane-3ß-ol. J. Amer. Chem. Soc. 75, 259 (1953).CrossRefGoogle Scholar
  201. 197.
    White, H. L.: Some Synthetic Esters of Germine. J. Amer. Chem. Soc. 73, 492 (1951).CrossRefGoogle Scholar
  202. 198.
    Wintersteiner, O.: Some Aspects of the Chemistry of Jervine and Veratramine In: Festschrift Arthur Stoll, pp. 166–176. Basel: Birkhäuser. 1957.Google Scholar
  203. 199.
    Wintersteiner, O.: Chemistry of the Veratrum Alkaloids. Record Chem. Progr. 14, 19 (1953).Google Scholar
  204. 200.
    Wintersteiner, O. and N. Hosansky: The Structural Correlation of Jervine and Veratramine. J. Amer. Chem. Soc. 74, 4474 (1952).CrossRefGoogle Scholar
  205. 201.
    Wintersteiner, O. and M. Moore: The Structure of Jervine. IV. The Sulfuric Acid-catalyzed Acetolysis of O,N-Diacetyljervine. J. Amer. Chem. Soc. 75, 4938 (1953).CrossRefGoogle Scholar
  206. 202.
    Wintersteiner, O. and M. Moore: Jervine. X. Quaternary Dihydrometoxazine Salts as Intermediates in the Jervisine Rearrangement. J. Amer. Chem. Soc. 78, 6193 (1956).CrossRefGoogle Scholar
  207. 203.
    Wintersteiner, O., M. Moore, J. Fried and B. Iselin: On the Structure of Jervine. Diacetyl-7-keto-jervine. Proc. Nat. Acad. Sci. (USA) 37, 333 (1951).CrossRefGoogle Scholar
  208. 204.
    Wintersteiner, O., M. Moore and N. Hosansxy: Degradation of Veratramine to Benzene-x,2,3,4-tetracarboxylic Acid. J. Amer. Chem. Soc. 75, 2781 (1953).CrossRefGoogle Scholar
  209. 205.
    Wintersteiner, O., M. Moore and B. M. Iselin; Jervine. V. Sulfuric Acid-catalyzed Acetolysis of Diacetyltetrahydrojervine. J. Amer. Chem. Soc. 76, 5609 (1954).CrossRefGoogle Scholar
  210. 206.
    Wolfrom, M. L. and J. M. Bobbitt: Periodate Oxidation of Cyclic 1,3­Diketones. J. Amer. Chem. Soc. 78, 2489 (1956).CrossRefGoogle Scholar
  211. 207.
    Woodward, R. B.: Lectures on the Chemistry of Natural Products — Veratrum Alkaloids. Harvard University, 1953 (see also Ref. 120).Google Scholar
  212. 208.
    Wright, C. R. A. and A. P. Luff: The Veratrum Alkaloids. J. Chem. Soc. (London) 33, 338 (1878).Google Scholar

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© Springer-Verlag in Vienna 1962

Authors and Affiliations

  • C. R. Narayanan
    • 1
  1. 1.PoonaIndia

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