Toward chemical libraries of annonaceous acetogenins. Total synthesis of trilobacin

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7640-7641

  Sinha, Subhash C ^a   Sinha, Anjana ^a   Yazbak, Ahmad ^a   Keinan, Ehud ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; TRILOBACIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029826078     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961286m     Document Type: Article

References (25)

1. (a) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237.
2. (b) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27.
3. (c) Figadére, B. Acc. Chem. Res. 1995, 28, 359.
4. (d) Koert, U. Synthesis 1995, 115.
5. (e) Hoppe, R.; Scharf, H.-D. Synthesis 1995, 1447.
6. (f) Zeng, L.; Zhang, Y.; McLaughlin, J. L. Tetrahedron Lett. 1996, 37, 5449.
7. Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, pp 249-310.
8. (a) Zhao, G.-X.; Hui, Y.-H.; Rupprecht, J. K.; McLaughlin J. L.; Wood, K. V. J. Nat. Prod. 1992, 55, 347.
9. (b) Zhao, G.-X.; Gu, Z.-M.; Zeng, L.; Chao, J.-F.; Kozlowski, J. F. Wood, K.V.; McLaughlin J. L. Tetrahedron 1995, 51, 7149.
10. Sinha, S. C.; Sinha-Bagchi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257.
11. For other synthetic approaches to bis-THF annonaceous acetogenins see: Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801 and references cited therein.
12. Sinha, S. C; Sinha-Bagchi, A.; Keinan, E. J. Am. Chem. Soc. 1995, 117, 1447.
13. Sinha, S. C; Keinan, E. J. Am. Chem. Soc. 1993, 115, 4891.
14. (a) Sinha, S. C; Keinan, E. J. Org. Chem. 1994, 59, 949.
15. (b) Sinha, S. C; Sinha-Bagchi, A.; Keinan, E. J. Org. Chem. 1993, 58, 7789.
16. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1984, 94, 2483.
17. (a) Tang, S.; Kennedy, R. M. Tetrahedron Lett. 1992, 33, 3729.
18. (b) Tang, S.; Kennedy, R. M. Tetrahedron Lett. 1992, 33, 5299.
19. (c) Tang, S.; Kennedy, R. M. Tetrahedron Lett. 1992, 33, 5303.
20. (d) Boyce, R. S.; Kennedy, R. M. Tetrahedron Lett. 1994, 35, 5133.
21. (e) McDonald, F. E.; Towne, T. B. J. Org. Chem. 1995, 60, 5750.
22. (a) Mitsunobu, O. Synthesis 1981, 1.
23. (b) Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017.
24. 6 (ref 6).
25. 13C NMR, and HRMS. For physical data of 10-17 see the supporting information.