Synthetic studies on spinosyn A. Convenient enantioselective construction of a suitably functionalized trans,anti-cis-decahydro-as-indacene intermediate via [3.3] sigmatropy and double configurational inversion

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1271-1274

  Paquette, Leo A ^a   Gao, Zhongli ^a   Ni, Zhijie ^a   Smith, Graham F ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INSECTICIDE; SPINOSYN A; UNCLASSIFIED DRUG;

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

EID: 0031584920     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00069-5     Document Type: Article

References (21)

1. (1) Isolation: (a) Jomon, K.; Kuroda, Y.; Ajisaka, M.; Sakai, H. J. Antibiot. 1972, 25, 271.
2. (b) Ito, S.; Hirata, Y. Tetrahedron Lett. 1972, 1181, 1185, 2257.
3. (c) Ito, S.; Hirata, Y. Bull. Chem. Soc. Jpn. 1977, 50, 227, 1813.
4. (2) Total synthesis: (a) Boeckman, R. K., Jr.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036.
5. (b) Paquette, L. A.; Macdonald, D.; Anderson, L. G.; Wright, J. J. Am. Chem. Soc. 1989, 111, 8037.
6. (c) Paquette, L. A.; Romine, J. L.; Lin, H. S.; Wright, J. J. Am. Chem. Soc. 1990, 112, 9284.
7. (d) Paquette, L. A.; Macdonald, D.; Anderson, L. G. J. Am. Chem. Soc. 1990, 112, 9292.
8. (e) Roush, W. R.; Wada, C. K. J. Am. Chem. Soc. 1994, 116, 2151.
9. (3) Isolation: Kirst, H. A., et al., ACS Symposium Series 504; American Chemical Society: Washington, DC, 1992; pp 214-225, and references cited therein. The names initially adopted for 2 (LY232105, A83543A, and lepicidin A) have been recently abandoned in favor of spinosyn A (Kirst, A.; communication dated June 7, 1994).
10. (4) Synthesis: Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1992, 114, 2260; 1993, 115, 4497.
11. (4) Synthesis: Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1992, 114, 2260; 1993, 115, 4497.
12. (5) See also: (a) Kurth, M. J.; Burns, D. H.; O'Brien, M. J. J. Org. Chem. 1984, 49, 731.
13. (b) Roush, W. R.; Works, A. B. Tetrahedron Lett. 1996, 37, 8065.
14. (6) Whitesell, J. K.; Minton, M. A. J. Am. Chem. Soc. 1987, 109, 6403.
15. (7) Jurecek, F.; Hanus, V.; Sedmera, P.; Antropiusova, H.; Mach, K. Tetrahedron 1979, 35, 1463.
16. (8) Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
17. 2.
18. (10) The resolution of racemic 4 was accomplished by means of Johnson's sulfoximine procotol [Johnson, C. R.; Zeller, J. R. J. Am. Chem. Soc. 1982, 104, 4021].
19. (11) Boeckman, R. K., Jr.; Potenza, J. C. Tetrahedron Lett. 1985, 26, 1411.
20. (12) Martin, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 4327.
21. 13C NMR, and high-resolution mass spectrometry and/or combustion analysis. The stereochemical assignments are reliably based on extensive NOE studies.