Synthetic studies on the perhydropyrrolo[2,1-j]quinoline marine alkaloids lepadiformine and cyclindricine C using a 2-azapentadienyl anion cycloaddition. Synthesis of 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C)

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3369-3372

  Pearson, William H ^a   Barta, Nancy S ^a   Kampf, Jeff W ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030907069     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00632-1     Document Type: Article

References (24)

1. Author to whom correspondence regarding the X-ray crystallographic determinations should be directed.
2. (a) Pearson, W. H.; Szura, D. P.; Harter, W. G. Tetrahedron Lett 1988, 29, 761-764.
3. (b) Pearson, W. H.; Szura, D. P.; Postich, M. J. J. Am. Chem. Soc. 1992, 114, 1329-1345.
4. (c) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1992, 57, 6354-6357.
5. (d) Pearson, W. H.; Stevens, E. P. Tetrahedron Lett. 1994, 35, 2641-2644.
6. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem 1994, 59, 5662-5671.
7. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176.
8. (g) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 12336-12337.
9. Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004.
10. (a) Blackman, A. J.; Li, C.; Modeless, D. C. R.; Skelton, B. W.; White, A. H. Tetrahedron 1993, 49, 8645-8656.
11. (b) Li, C.; Blackman, A. J. Aust. J. Chem. 1994, 47, 1355-1361.
12. (c) Li, C.; Blackman, A. J. Aust. J. Chem. 1995, 48, 955-965.
13. Biard, J. F.; Guyot, S.; Roussakis, C.; Verbist, J. F.; Vercauteren, J.; Weber, J. F.; Boukef, K. Tetrahedron Lett. 1994, 35, 2691-2694.
14. Approach of the alkene from the face of the 2-azapentadienyl anion opposite to the 2-alkyl group is precedented in the diasteroselective alkylation of exocyclic enolates involving 1,2-asymmetric induction, where A(l,3) strain is known to force the 2-alkyl group into the axial position. See: (a) Evans, D. A. In Asymmetric Synthesis; J. D. Morrison, Ed.; Academic Press: New York, 1984; Vol. 3; pp 1-110.
15. (b) Krapcho, A. P.; Dundulis, E. A. J. Org. Chem 1980, 45, 3236-3245.
16. Stork, G.; Brizzolara, A.; Landesman, J.; Szmuskovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
17. (a) Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1978, 27, 2417.
18. (b) Okazoe, T.; Hibino, J.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
19. Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668.
20. (a) Nahm, S.; Weinreb, S. M.; Tetrahedron Lett. 1981, 22, 3815.
21. (b) Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171.
22. Chong, J. M.; Park, S. B. J. Org. Chem 1992, 57, 2220-2222.
23. A separate experimental run was performed, starting with the phthalimide 11 and proceeding to 17 without purification of intermediates, resulting in a 1.8% overall yield (unoptimized). The Raney nickel step was estimated to proceed in about 28% yield.
24. The anions 6E and 6Z are shown as the "W" geometry. The cycloadduct 14 might also also arise from the "U" geometry of 6Z, as suggested by a referee. However, at least for 2-azaallyl anions, the "W" form appears to be the most likely. See reference 2c above and the references cited therein.