A simple convergent approach to the synthesis of the antiviral agent virantmycin

Organic Letters

Volumn 1, Issue 5, 1999, Pages 823-824

  Steinhagen, Henning ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000127173     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9908575     Document Type: Article

References (13)

1. Ōmura, S., Nakagawa, A. Tetrahedron Lett. 1981, 22, 2199.
2. The naturally occurring form of virantmycin has not yet been synthesized; for syntheses of (±)- or ent-virantmycin see: (a) Hill, M. L.; Raphael, R. A. Tetrahedron Lett. 1986, 27, 1293.
3. (b) Hill, M. L.; Raphael, R. A. Tetrahedron 1990, 46, 4587.
4. (c) Morimoto, Y.; Matsuda, F.; Shirahama, H. Synlett 1991, 202.
5. (d) Morimoto, Y.; Matsuda, F.; Shirahama, H. Tetrahedron 1996, 52, 10609.
6. Steinhagen, H.; Corey, E. J. Angew. Chem., Int. Ed. 1999, 38, 1928.
7. Nowick, J. S.; Holmes, D. L.; Noronha, G.; Smith, E. M.; Nguyen, T. M.; Huang, S.-L. J. Org. Chem. 1996, 61, 3929.
8. (a) Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254.
9. (b) Wang, Z.; Lu, X. Tetrahedron Lett. 1997, 29, 5213.
10. (c) Wang, Z.; Lu, X. J. Chem. Soc., Chem. Commun. 1996, 535.
11. Any E-isomeric chloroolefin which may be present in the starting material 8 is lost in this step because it does not undergo cyclization under the conditions of the conversion 8 → 10.
12. Kim, S.; Ahn, K. H. J. Org. Chem. 1984, 49, 1717.
13. Graciously provided by Prof. Satoshi Omura, to whom we are very grateful.