Chiral and Achiral Formamidines in Synthesis. The First Asymmetric Route to (-)-Yohimbone and an Efficient Total Synthesis of (±)-Yohimbone

Journal of the American Chemical Society

Volumn 110, Issue 14, 1988, Pages 4778-4787

  Meyers, A I ^a   Miller, Donald B ^a   White, Franklin H ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

UNCLASSIFIED DRUG; YOHIMBONE;

DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0023726526     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00222a041     Document Type: Article

References (35)

1. For a review of earlier studies, see: Meyers, A. I. Aldrichimica Acta 1985, 18, 59. Meyers, A. I. Lect. Heterocycl. Chem. 1984, 7, 75.
2. Meyers, A. I.; Loewe, M. F. Tetrahedron Lett. 1984, 25, 2641. Meyers, A. I.; Hellring, S. J. Org. Chem. 1982, 47, 2229.
3. Meyers, A. I.; Hellring, S.; ten Hoeve, W. Tetrahedron Lett. 1981, 22, 5115.
4. Meyers, A. I.; Sohda, T.; Loewe, M. F. J. Org. Chem. 1986, 51, 3108.
5. Loewe, M. F.; Meyers, A. I. Tetrahedron Lett. 1985, 26, 1985.
6. Meyers, A. I.; Bailey, T. R. J. Org. Chem. 1986, 51, 872.
7. Meyers, A. I.; Dickman, D. A.; Bailey, T. R. J. Am. Chem. Soc. 1985, 107, 7974.
8. Meyers, A. I.; Bos, M.; Dickman, D. A. Angew. Chem., Int. Ed. Engl. 1984, 23, 458. Meyers, A. I.; Bos, M.; Dickman, D. A. Tetrahedron 1987, 43, 5095.
9. Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113.
10. Meyers, A. I.; Rieker, W. F.; Fuentes, L. M. J. Am. Chem. Soc. 1983, 105, 2082. Al-Aseer, M.; Beak, P.; Hay, D.; Kempf, D. J.; Mills, S.; Smith, S. G. J. Am. Chem. Soc. 1983, 105, 2080.
11. Meyers, A. I.; Dickman, D. A. J. Am. Chem. Soc. 1987, 109, 1263. Gawley, R. E. J. Am. Chem. Soc. 1987, 109, 1265.
12. For review on the yohimboid alkaloids, see: (a) The Alkaloids, Chemistry and Physiology; Manske, R. H. F., Ed.; Academic: New York, 1981; Vol. 20.
13. Saxton, J. E. In Specialist Periodical Reports, The Alkaloids; The Royal Society of Chemistry, Burlington House: London, 1983; Vol. 13, pp 221–237. See also in Vol. 1–12
14. Cordell, G. A Introduction to Alkaloids, A Biogenetic Approach; Wiley-Interscience: New York, 1981; pp 574–832.
15. Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6214. For a thorough accumulation of pertinent references dealing with the yohimboid class of alkaloids, consult this article.
16. Wender, P. M.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157; Heterocycles, 1987, 25, 263.
17. Benson, W.; Winterfeldt, E. Chem. Ber. 1979, 112, 1913.
18. Rischke, H.; Wilcock, J.; Winterfeldt, E. Chem. Ber. 1973, 106, 3106.
19. Ahmad, V. U.; Feuerhard, K. H.; Winterfeldt, E. Chem. Ber. 1977, 110, 3624.
20. Okamura, K.; Yamada S.-I. Chem. Pharm. Bull. 1978, 26, 2305.
21. Pirkle, W. H.; Welch, C. J.; Mahler, G. S.; Meyers, A. I.; Fuentes, L. M.; Bös, M. J. Org. Chem. 1984, 49, 2504.
22. Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983.
23. Guindon, Y.; Yoakim, C.; Morton, H. E. J. Org. Chem. 1984, 49, 3912.
24. Larsen, S. D.; Grieco, P. A.; Fobare, W. F. J. Am. Chem. Soc. 1986, 108, 3512.
25. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
26. Bartlett, V.-L.; Dastoor, N. J.; Hrbek, J., Jr.; Klyne, W.; Schmid, H.; Snatzke, G. Helv. Chim. Acta 1971, 54, 1238.
27. Morrison, G. C.; Waite, R. O.; Shavel, J. J. J. Heterocyl. Chem. 1971, 5, 1025.
28. Swan, G. A. J. Chem. Soc. 1950, 1534.
29. X-ray structure of 1 with all attending structrual parameters are contained in the supplementary material.
30. Autrey, R. L.; Scullard, P. W. Chem. Commun. 1966, 841.
31. Grieco, P. A.; Fobare, W. F. Chem. Commun. 1987, 185.
32. Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamora, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. Kitamura, M.; Hsiao, Y.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4829.
33. Ho, B. T.; Walker, K. E. Org. Synth. 1968, 51, 136.
34. Dickman, D. A.; Bos, M.; Meyers, A. I. Org. Synth., in press.
35. Czantay, C.; Honty, K.; Toke, L.; Szabo, L. Chem. Ber. 1976, 109, 1737.