Total synthesis of (±)-herbindole B and (±)-cis-trikentrin B

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1215-1218

  Jackson, Stephen K ^a   Banfield, Scott C ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HERBINDOLE B; INDOLE DERIVATIVE; PYRROLE DERIVATIVE; QUINONE DERIVATIVE; TRIKENTRIN B; UNCLASSIFIED DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INDOLE ALKALOID;

ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; SUBSTITUTION REACTION; ANIMAL; AXINELLA; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ANIMALS; AXINELLA; CATALYSIS; CYCLIZATION; INDICATORS AND REAGENTS; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 17444376067     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047498k     Document Type: Article

References (26)

1. Herb, R.; Carroll, A. R.; Yoshida, W. Y.; Scheuer, P. J.; Paul, V. J. Tetrahedron 1990, 46, 3089.
2. Capon, R. J.; Macleod, J. K.; Scammells, P. J. Tetrahedron 1986, 42, 6545.
3. (a) Muratake, H.; Mikawa, A.; Seino, T.; Natsume, M. Chem. Pharm. Bull. 1994, 42, 854.
4. (b) Muratake, H.; Mikawa, A.; Seino, T.; Natsume, M. Chem. Pharm. Bull. 1994, 42, 846.
5. Macleod, J. K.; Monaham, L. C. Tetrahedron Lett. 1988, 29, 391.
6. Blechert, S.; Wiedenau, P.; Monse, B. Tetrahedron 1995, 51, 1167.
7. Boger, D. L.; Zhang, M. J. Am. Chem. Soc. 1991, 113, 4230.
8. (a) Natsume, M.; Muratake, H. Tetrahedron Lett. 1989, 30, 5771.
9. (b) Natsume, M.; Muratake, H.; Seino, T. Tetrahedron Lett. 1993, 34, 4815.
10. Kanematsu, K.; Lee, M.; Ikeda, I.; Kawabe, T.; Mori, S. J. Org. Chem. 1996, 61, 3406.
11. Banfield, S. C.; Kerr, M. A. Can. J. Chem. 2004, 82, 131.
12. (b) Kerr, M. A. Synlett 1995, 1165.
13. (a) Banfield, S. C.; England, D. B.; Kerr, M. A. Org. Lett. 2001, 3, 3325.
14. (b) Zawada, P. V.; Banfield, S. C.; Kerr, M. A. Synlett 2003, 971.
15. (a) Pleininger, H.; Suhr, K. Chem. Ber. 1956, 89, 270.
16. (b) Pleininger, H.; Volkl, A. Chem. Ber. 1976, 109, 2121.
17. For applications of the Pleininger indolization, see: (c) Kraus, G. A.; Yue, S.; Sy, J. J. Org. Chem. 1985, 50, 284. (d) Maehr, H.; Smallheer, J. J. Am. Chem. Soc. 1985, 107, 2943. (e) Tichenor, M. S.; Kastrinsky, D. B.; Boger D. L. J. Am. Chem. Soc. 2004, 26, 8396.
18. For applications of the Pleininger indolization, see: (c) Kraus, G. A.; Yue, S.; Sy, J. J. Org. Chem. 1985, 50, 284. (d) Maehr, H.; Smallheer, J. J. Am. Chem. Soc. 1985, 107, 2943. (e) Tichenor, M. S.; Kastrinsky, D. B.; Boger D. L. J. Am. Chem. Soc. 2004, 26, 8396.
19. For applications of the Pleininger indolization, see: (c) Kraus, G. A.; Yue, S.; Sy, J. J. Org. Chem. 1985, 50, 284. (d) Maehr, H.; Smallheer, J. J. Am. Chem. Soc. 1985, 107, 2943. (e) Tichenor, M. S.; Kastrinsky, D. B.; Boger D. L. J. Am. Chem. Soc. 2004, 26, 8396.
20. For an excellent preparative procedure of 9 from 3-methyl-4-nitrophenol, see: Todd, M. H.; Oliver, S. F.; Abell, C. Org. Lett. 1999, 1, 1149.
21. For the preparation of PIBA, see: Smith, J. G. Fieser and Fieser's Reagents for Organic Synthesis; Wiley: Toronto, 1990; Vol. 1, p 508.
22. Alexakis, A.; Duffault, J. M. Tetrahedron 1988, 29, 6243.
23. 1H NMR were used to determine the trans/cis ratio.
24. Fujimoto, Y.; Tatsuno, T. Tetrahedron Lett. 1976, 37, 3325.
25. Yasuhara, A.; Sakamoto, T. Tetrahedron Lett. 1998, 39, 595.
26. Zhong, Y. L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622.