Convergent syntheses of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners

Chemical Communications

Volumn , Issue 2, 1997, Pages 207-208

  Banwell, Martin G ^a   Flynn, Bernard L ^a   Hamel, Ernest ^b   Hockless, David C R ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; LAMELLARIN O; LAMELLARIN Q; LUKIANOL A; NATURAL PRODUCT; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0031038322     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a606793j     Document Type: Article

References (25)

1. R. J. Andersen, D. J. Faulkner, H. Cun-heng, G. D. van Duyne and J. Clardy, J. Am. Chem. Soc., 1985, 107, 5492.
2. N. Lindquist, W. Fenical, G. D. van Duyne and J. Clardy, J. Org. Chem., 1988, 53, 4570.
3. A. R. Carroll, B. F. Bowden and J. C. Coll, Aust. J. Chem., 1993, 46, 489.
4. S. Urban, M. S. Butler and R. J. Capon, Aust. J. Chem., 1994, 47, 1919.
5. S. Urban, L. Hobbs, J. N. A. Hooper and R. J. Capon, Aust. J. Chem., 1995, 48, 1491.
6. W. Y. Yoshida, K. K. Lee, A. R. Carroll and P. J. Scheuer, Helv. Chim. Acta, 1992, 75, 1721.
7. J. A. Palermo, M. Florencia Rodriguez Brasco and A. M. Seldes, Tetrahedron, 1996, 52, 2727.
8. A. Rudi, I. Goldberg, Z. Stein, F. Frolow, Y. Benayahu, M. Schleyer and Y. Kashman, J. Org. Chem., 1994, 59 999.
9. R. T. Brown, B. W. Fox, J. A. Hadfield, A. T. McGown, S. P. Mayalarp, G. R. Pettit and J. A. Woods, J. Chem. Soc., Perkin Trans. 1, 1995, 577 and references cited therein.
10. M. G. Banwell, Pure Appl. Chem., 1996, 68, 539 and references cited therein.
11. For an example of the successful hybridisation of the combretastatin and colchicine structures see C. J. Andres, J. E. Bernardo, Q. Yan, S. B. Hastie and T. L. Macdonald, Bioorg. Med. Chem. Lett., 1993, 3, 565.
12. During the course of the work described here a very different approach to lukianol A and the dimethyl ether of lamellarin O was reported (A. Fürstner, H. Weintritt and A. Hupperts, J. Org. Chem., 1995, 60, 6637).
13. Steglich et al. have reported a biomimetic synthesis of polycitrin A (A. Terpin, K. Polborn and W. Steglich, Tetrahedron, 1995, 51, 9941).
14. (a) J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508;
15. (b) T. N. Mitchell, Synthesis, 1992, 803.
16. A. Suzuki, Pure Appl. Chem., 1994, 66, 213 and references cited therein.
17. (a) E. Negisihi, T. Takahashi and A. O. King, Org. Synth., 1987, 66, 67;
18. (b) P. Knochel and R. D. Singer, Chem. Rev., 1993, 93, 2117.
19. For discussions of this matter see (a) A. Minato, K. Tamao, T. Hayashi, K. Suzuki and M. Kumada, Tetrahedron Lett., 1981, 22, 5319; (b) J. Wang and A. I. Scott, Tetrahedron Lett., 1995, 36, 7043; (c) C. K. Chang and N. Bag, J. Org. Chem., 1995, 60, 7030 and references cited therein. Also see K. Takahashi, A. Gunji, K. Yanagi and M. Miki, J. Org. Chem., 1996, 61, 4784.
20. For discussions of this matter see (a) A. Minato, K. Tamao, T. Hayashi, K. Suzuki and M. Kumada, Tetrahedron Lett., 1981, 22, 5319; (b) J. Wang and A. I. Scott, Tetrahedron Lett., 1995, 36, 7043; (c) C. K. Chang and N. Bag, J. Org. Chem., 1995, 60, 7030 and references cited therein. Also see K. Takahashi, A. Gunji, K. Yanagi and M. Miki, J. Org. Chem., 1996, 61, 4784.
21. For discussions of this matter see (a) A. Minato, K. Tamao, T. Hayashi, K. Suzuki and M. Kumada, Tetrahedron Lett., 1981, 22, 5319; (b) J. Wang and A. I. Scott, Tetrahedron Lett., 1995, 36, 7043; (c) C. K. Chang and N. Bag, J. Org. Chem., 1995, 60, 7030 and references cited therein. Also see K. Takahashi, A. Gunji, K. Yanagi and M. Miki, J. Org. Chem., 1996, 61, 4784.
22. For discussions of this matter see (a) A. Minato, K. Tamao, T. Hayashi, K. Suzuki and M. Kumada, Tetrahedron Lett., 1981, 22, 5319; (b) J. Wang and A. I. Scott, Tetrahedron Lett., 1995, 36, 7043; (c) C. K. Chang and N. Bag, J. Org. Chem., 1995, 60, 7030 and references cited therein. Also see K. Takahashi, A. Gunji, K. Yanagi and M. Miki, J. Org. Chem., 1996, 61, 4784.
23. B. L. Bray, P. H. Mathies, R. Naef, D. R. Solas, T. T. Tidwell, D. R. Artis and J. M. Muchowski, J. Org. Chem., 1990, 55, 6317.
24. K. S. Chan, X. Zhou, M. T. Au and C. Y. Tam, Tetrahedron, 1995, 51, 3129.
25. B. F. Bowden, R. W. Read and W. C. Taylor, Aust. J. Chem., 1981, 34, 799.