Total synthesis of (±)-phomactin G, a platelet activating factor antagonist from the marine fungus Phoma sp.

Organic and Biomolecular Chemistry

Volumn 2, Issue 4, 2004, Pages 466-473

  Goldring, William P D ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CARBON; CHEMICAL BONDS; ESTERS; FUNGI; IODINE; ISOMERIZATION; KETONES; METABOLITES; OXIDATION; STEREOCHEMISTRY;

MACROCYCLIZATION; PYRAN RING;

AROMATIC COMPOUNDS;

FUNGI; PHOMA;

EPOXIDE; PHOMACTIN G; THROMBOCYTE ACTIVATING FACTOR;

ARTICLE; ASCOMYCETES; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

ASCOMYCOTA; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; PLATELET ACTIVATING FACTOR;

EID: 1342281362     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b314816e     Document Type: Article

References (15)

1. M. Sugano, A. Sato, Y. Iijima, K. Furuya, H. Kuwano and T. Hata, J. Antibiot., 1995, 48, 1188-1190.
2. M. Sugano, A. Sato, Y. Iijima, T. Oshima, K. Furuya, H. Kuwano, T. Hata and H. Hanzawa, J. Am. Chem. Soc., 1991, 113, 5463-5464.
3. M. Chu, I. Truumees, I. Gunnarsson, W. R. Bishop, W. Kreutner, A. C. Horan, M. G. Patel, V. P. Gullo and M. S. Puar, J. Antibiot., 1993, 46, 554-563.
4. (a) W. P. D. Goldring and G. Pattenden, Chem. Commun., 2002, 1736-1737;
5. (b) C. M. Diaper, W. P. D. Goldring and G. Pattenden, Org. Biomol. Chem., 2003, 1, 3949-3956.
6. J. W. C. Cheing, W. P. D. Goldring and G. Pattenden, Chem. Commun., 2003, 2788-2789.
7. M. Sugano, A. Sato, Y. Iijima, K. Furuya, H. Haruyama, K. Yoda and T. Hata, J. Org. Chem., 1994, 59, 564-569. For a synthesis of phomactin D see: H. Miyaoka, Y. Saka, S. Miura and Y. Yamada, Tetrahedron Lett., 1996, 37, 7107-7110.
8. M. Sugano, A. Sato, Y. Iijima, K. Furuya, H. Haruyama, K. Yoda and T. Hata, J. Org. Chem., 1994, 59, 564-569. For a synthesis of phomactin D see: H. Miyaoka, Y. Saka, S. Miura and Y. Yamada, Tetrahedron Lett., 1996, 37, 7107-7110.
9. (a) K. M. Foote, M. John and G. Pattenden, Synlett, 2001, 365-368;
10. (b) K. M. Foote, C. J. Hayes, M. P. John and G. Pattenden, Org. Biomol. Chem., 2003, 1, 3917-3948.
11. D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 1991, 113, 7277-7287.
12. Selective NOE enhancements measured for 16 were observed between H-16a and H-2, and H-7 and H-3.
13. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440-467.
14. K. B. Sharpless and R. C. Michaelson, J. Am. Chem. Soc., 1973, 95, 6136-6137.
15. W. Adam, Y.-Y. Chan, D. Cremer, J. Gauss, D. Scheutzow and M. Schindler, J. Org. Chem., 1987, 52, 2800-2803.