Total synthesis of the cytotoxic threo, trans, erythro, cis, threo Annonaceous acetogenin trilobin

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 971-975

  Marshall, James A ^a   Jiang, Hongjian ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; CYTOTOXIC AGENT; TRILOBINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033525058     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982057y     Document Type: Article

References (27)

1. (a) Zhao, G.-X.; Gu, Z.-M.; Zeng, L. Chao, J.-F.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L. Tetrahedron 1995, 51, 7149.
2. (b) Reviews: Cavé, A.; Figadére, B.; Laureno, A.; Cortes, D. In Progress in the Chemistry of Natural Products; Herz, W., Kirby, G.-W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.; Springer: New York, 1997; Vol. 70, pp 81-288.
3. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275.
4. (c) For leading references to recent synthetic efforts in this area, see Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801. Yazbec, A.; Sinha, S. C.; Keinan, E. J. Org. Chem. 1998, 63, 5863.
5. (c) For leading references to recent synthetic efforts in this area, see Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801. Yazbec, A.; Sinha, S. C.; Keinan, E. J. Org. Chem. 1998, 63, 5863.
6. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 4247.
7. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1997, 62, 5989.
8. Marshall, J. A.; Chen, M.; J. Org. Chem. 1997, 62, 5996.
9. Marshall, J. A.; Hinkle, K. W. Tetrahedron Lett. 1998, 39, 1303.
10. 1a
11. Marshall, J. A.; Jiang, H. J. Org. Chem. 1998, 63, 7066.
12. Sinha, S. C.; Sinha, A.; Yazbec, A.; Keinan, E. J. Org. Chem. 1996, 61, 7640.
13. 1H NMR analysis of the (R)- and (S)-O-methyl mandelates as described in the Ph.D. Thesis of Kevin Hinkle, University of Virginia, 1998. Copies of these spectra are included in the Supporting Information.
14. Baska, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 17, 4171.
15. 2 For details see the Supporting Information.
16. Marshall, J. A.; Jiang, H. Tetrahedron Lett. 1998, 39, 1493.
17. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156. Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
18. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156. Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
19. 2. For details, see the Supporting Information.
20. Liu, S.-H. J. Org. Chem. 1977, 42, 3209.
21. Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895.
22. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. D. J. Org. Chem. 1986, 51, 2370.
23. Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180.
24. Yao, Z.-J.; Wu, Y.-L. Tetrahedron Lett. 1994, 35, 157.
25. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
26. Duret, P.; Figadère, B.; Hocquemiller, R.; Cavé, A. Tetrahedron Lett. 1997, 38, 8849.
27. Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 2.4. Butenolide i was prepared as described in ref 4. This experiment was performed in our laboratory by Dr. Paul Lobben.