Indole diterpenoid synthetic studies. Construction of the heptacyclic core of (-)-nodulisporic acid D

Organic Letters

Volumn 8, Issue 8, 2006, Pages 1669-1672

  Smith III, Amos B ^a   Davulcu, Akin H ^a   Kürti, László ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; INDOLE DERIVATIVE; NODULISPORIC ACID D;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

DITERPENES; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33646456752     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0602912     Document Type: Article

References (21)

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2. Ondeyka, J. G.; Helms, G. L.; Hensens, O. D.; Goetz, M. A.; Zink, D. L.; Tsipouras, A.; Shoop, W. L.; Slayton, L.; Dombrowski, A. W.; Polishook, J. D.; Ostlind, D. A.; Tsou, N. N.; Ball, R. G.; Singh, S. B. J. Am. Chem. Soc. 1997, 119, 8809.
3. Ludmerer, S. W.; Warren, V. A.; Williams, B. S.; Zheng, Y. C.; Hunt, D. C.; Ayer, M. B.; Wallace, M. A.; Chaudhary, A. G.; Egan, M. A.; Meinke, P. T.; Dean, D. C.; Garcia, M. L.; Cully, D. F.; Smith, M. M. Biochemistry 2002, 41, 6548.
4. Singh, S. B.; Ondeyka, J. G.; Jayasuriya, H.; Zink, D. L.; Ha, S. N.; Dahl-Roshak, A. M.; Greene, J.; Kim, J. A.; Smith, M. M.; Shoop, W.; Tkacz, J. S. J. Nat. Prod. 2004, 67, 1496.
5. For representative studies, see: (a) Smith, A. B., III; Mewshaw, R. E. J. Am. Chem. Soc. 1985, 107, 1796.
6. (b) Mewshaw, R. E.; Taylor, M. D.; Smith, A. B., III. J. Org. Chem. 1989, 54, 3449.
7. (c) Smith, A. B., III; Sunazuka, T.; Leenay, T. L.; Kingery-Wood, J. J. Am. Chem. Soc. 1990, 112, 8197.
8. (d) Smith, A. B., III; Kingery-Wood, J.; Leenay, T. L.; Nolen, E. G., Jr.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438.
9. (e) Smith, A. B., III; Kanoh, N.; Minakawa, N.; Rainier, J. D.; Blase, F. R.; Hartz, R. A. Org. Lett. 1999, 1, 1263.
10. (f) Smith, A. B., III; Kanoh, N.; Ishiyama, H.; Hartz, R. A. J. Am. Chem. Soc. 2000, 114, 1438.
11. Smith, A. B., III; Visnick, M.; Haseltine, J. N.; Sprengler, P. A. Tetrahedron 1986, 42, 2957.
12. Smith, A. B., III; Davulcu, A. H.; Kürti, L. Org. Lett. 2006, 8, 1665.
13. Evans, D. A.; Miller, S. J.; Ennis, M. D. J. Org. Chem. 1993, 58, 471.
14. Smith, A. B., III; Cui, H. Org. Lett. 2003, 5, 587.
15. (a) Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253.
16. (b) Enders, D.; Eichenauer, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 549.
17. Farina, V.; Krishnamurthy, V.; Scott, W. J. In The Stille Reaction; John Wiley and Sons: New York, 1998; p 20.
18. For a similar sequence see: Smith, A. B., III; Ishiyama, H.; Cho, Y. S.; Ohmoto, K. Org. Lett. 2001, 3, 3967.
19. The enantiomeric excess was determined by reverse-phase HPLC employing a chiral column. See Supporting Information.
20. Kelly, T. R.; Li, Q.; Bhushan, A. Tetrahedron Lett. 1990, 31, 161.
21. The alkyllithium-initiated anionic polymerization of styrenes is well-known; see: Wakefield, B. J. The Chemistry of Organolithium Compounds; Pergamon: Oxford, 1974. Indeed, 5-vinyl-2-methylaniline undergoes facile anionic polymerization upon exposure to s-BuLi.