A novel approach to iboga alkaloids: Total synthesis of (±)-ibogamine and (±)-epi-ibogamine

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8289-8292

  Henry, Kenneth J ^a   Grieco, Paul A ^a   DuBay, William J ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; IBOGAMINE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030580371     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01939-9     Document Type: Article

References (25)

1. 1. Büchi, G.; Coffen, D.L.; Kocsis, K.; Sonnet, P.E.; Ziegler, F.E. J. Am. Chem. Soc. 1965, 87, 2073.
2. Büchi, G.; Coffen, D.L.; Kocsis, K.; Sonnet, P.E.; Ziegler, F.E. J. Am. Chem. Soc. 1966, 88, 3099.
3. 2. For previous syntheses of ibogamine, see: a) Sallay, S.I. J. Am. Chem. Soc. 1967, 89, 6762.
4. b) Nagata, W.; Hirai, S.; Okumura, T.; Kawata, K. J. Am. Chem. Soc. 1968, 90, 1650.
5. c) Ikezaki, M.; Wakamatsu, T.; Ban, Y. J. Chem. Soc., Chem. Commun. 1969, 88.
6. d) Rosenmund, P.; Haase, W.H.; Bauer, J.; Frische, R. Chem. Ber. 1975, 108, 1871.
7. e) Trost, B.M.; Godleski, S.A.; Genet, J.P. J. Am. Chem. Soc. 1978, 100, 3930.
8. f) Atta-ur-Rahman; Beisler, J.A.; Harley-Mason, J. Tetrahedron 1980, 36, 1063.
9. g) Imanishi, T.; Yagi, N.; Hanaoka, M. Chem. Pharm. Bull. 1985, 33, 4202.
10. h) Huffman, J.W.; Shanmugasundaram, G.; Sawdaye, R.; Raveendranath, P.C.; Desai, R.D. J. Org. Chem. 1985, 50, 1460.
11. i) Kuehne, M.E.; Reider, P.J. J. Org. Chem. 1985, 50, 1464.
12. 3. Kuehne, M.E.; Lambert, B.F. J. Am. Chem. Soc. 1959, 81, 4278.
13. 4. Gemal, A.L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.
14. 5. Freter, K.; Weissbach, H.; Redfield, B.; Udenfriend, S.; Witkop, B. J. Am. Chem. Soc. 1958, 80, 983.
15. 6. For the reactions of allylic alcohols with indoles see: a) Pearson, W.H.; Schkeryantz, J.M. J. Org. Chem. 1992, 57, 2986.
16. b) Henry, K.J., Jr.; Grieco, P.A. J. Chem. Soc. Chem. Commun. 1993, 510.
17. 11)2] as a catalyst for the conjugate addition of silyl ketene acetals to α,β-unsaturated carbonyl compounds, see: DuBay, W.J.; Grieco, P.A.; Todd, L.J. J. Org. Chem. 1994, 59, 6898.
18. (b) Grieco, P.A.; DuBay, W.J.; Todd, L.J. Tetrahedron Lett. in press.
19. 8. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Japan 1977, 50, 2773.
20. 9. Dess, D.B.; Martin, J.C. J. Am. Chem. Soc. 1991, 113, 7277.
21. 10. For use of the hypervalent iodine species 10 in organic synthesis, see: VanderRoest, J.M.; Grieco, P.A. J. Am. Chem. Soc. 1993, 115, 5841.
22. Grieco, P.A.; Collins, J.L.; Moher, E.D.; Fleck, T.J.; Gross, R.S. J. Am. Chem. Soc. 1993, 115, 6078.
23. 11. Jackson, A.E.; Johnstone, R.A.W. Synthesis 1976, 685.
24. 12. Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Chem. Soc. 1971, 93, 2897. Kursanov, D.N.; Parnes, Z.N.; Loim, N.M. Synthesis 1974, 635.
25. 12. Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Chem. Soc. 1971, 93, 2897. Kursanov, D.N.; Parnes, Z.N.; Loim, N.M. Synthesis 1974, 635.