Total synthesis of auripyrones A and B and determination of the absolute configuration of auripyrone B

Angewandte Chemie - International Edition

Volumn 49, Issue 13, 2010, Pages 2401-2405

  Hayakawa, Ichiro ^a   Takemura, Takuma ^a   Fukasawa, Emi ^a   Ebihara, Yuta ^a   Sato, Natsuki ^a   Nakamura, Takayasu ^a   Suenaga, Kiyotake ^a,b   Kigoshi, Hideo ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Aldol reactions; Auripyrones; Diastereoselectivity; Natural products; Total synthesis

Indexed keywords

KETONES; STEREOSELECTIVITY;

ALDOL REACTIONS; AURIPYRONES; DIASTEREO-SELECTIVITY; NATURAL PRODUCTS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; AURIPYRONE A; AURIPYRONE B; PYRONE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; MOLECULAR STRUCTURE; PYRONES; SPIRO COMPOUNDS;

EID: 77953516606     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906662     Document Type: Article

References (21)

1. S. Yamamura, S. Nishiyama, Bull. Chem. Soc. Jpn. 1997, 70, 2025-2037.
2. J. E. Biskupiak, C. M. Ireland, Tetrahedron Lett. 1985, 26, 4307-4310.
3. D. C. Manker, D. J. Faulkner, J. Org. Chem. 1989, 54, 5374-5377.
4. M. Carbone, M. Gavagnin, C. A. Mattia, C. Lotti, F. Castelluc-cio, B. Pagano, E. Mollo, Y-W. Guo, G. Cimino, Tetrahedron 2009, 65, 4404-4409.
5. K. Suenaga, H. Kigoshi, K. Yamada, Tetrahedron Lett. 1996, 37, 5151-5154.
6. T. Lister, M. V. Perkins, Angew. Chem. 2006, 118, 2622-2626;
7. Angew. Chem. Int. Ed. 2006, 45, 2560-2564.
8. M. E. Jung, R. Salehi-Rad, Angew. Chem 2009, 121, 8922-8925;
9. Angew. Chem. Int. Ed. 2009, 48, 8766-8769.
10. T. Sengoku, T. Takemura, E. Fukasawa, I. Hayakawa, H. Kigoshi, Tetrahedron Lett. 2009, 50, 325-328.
11. H. Arimoto, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1990, 31, 5619-5620.
12. M. J. Gaunt, A. S. Jessiman, P. Orsini, R. T. Huw, D. F. Hook, S. V. Ley, Org. Lett. 2003, 5, 4819-4822.
13. H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 293-294.
14. The determination of the absolute stereochemistry of 19 is given in the Supporting Information.
15. R. Pappo, D S. Allen, R. U. Lemieux, W. S. Johnson, J. Org. Chem. 1956, 27, 478-479.
16. J. D. White, G. L. Bolton, A. P. Dantanarayana, C. M. J. Fox, R. N. Hiner, R. W Jackson, K. Sakuma, U. S. Warrier, J. Am. Chem. Soc. 1995, 117, 1908-1939.
17. a) I. Paterson, R. D. Tiller, Tetrahedron Lett. 1991, 32, 1749-1752;
18. b) I. Paterson, M. A. Lister, G. R. Ryan, Tetrahedron Lett. 1992, 55, 4233-4236.
19. N. M. Kelly, R. G. Reid, C. L. Willis, P. L. Winton, Tetrahedron Lett. 1996, 57, 1517-1520.
20. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
21. 1H NMR spectra of synthetic and natural samples of auripyr-one B are shown in the Supporting Information.