A Concise Synthesis of Fumagillol

Authors

David A. Vosburg, Harvey Mudd CollegeFollow
Sven Weiler, The Scripps Research Institute
Erik J. Sorensen, The Scripps Research Institute

Document Type

Article

Department

Chemistry (HMC)

Publication Date

1999

Abstract

A 13-step synthesis of (±)-fumagillol (1), the direct precursor of the potent angiogenesis inhibitors TNP-470 and fumagillin, from crotonaldehyde, diethylamine, and acrolein (see the scheme) has been achieved. The synthesis features a remarkable hetero-Claisen rearrangement. Small-molecule inhibitors of angiogenesis are promising chemotherapeutic agents for the treatment of cancer and inflammatory diseases.

Rights Information

© 1999 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany

DOI

10.1002/(SICI)1521-3773(19990401)38:7<971::AID-ANIE971>3.0.CO;2-W

Recommended Citation

“A concise synthesis of fumagillol,” Vosburg, D.A.; Weiler, S.; Sorensen, E.J. Angew. Chem. 1999, 111, 1024-1027; Angew. Chem. Int. Ed. 1999, 38, 971-974. DOI: 10.1002/(SICI)1521-3773(19990401)38:7<971::AID-ANIE971>3.0.CO;2-W