A concise synthesis of fumagillol

David A. Vosburg; Sven Weiler; Erik J. Sorensen

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

A concise synthesis of fumagillol

David A. Vosburg, Sven Weiler, Erik J. Sorensen

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

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.

Original language	English (US)
Pages (from-to)	971-974
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	38
Issue number	7
DOIs	https://doi.org/10.1002/(SICI)1521-3773(19990401)38:7<971::AID-ANIE971>3.0.CO;2-W
State	Published - Apr 1 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

Keywords

Angiogenesis
Antitumor agents
Fumagillin
Natural products
Total synthesis

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

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AU - Weiler, Sven

AU - Sorensen, Erik J.

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AB - 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.

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KW - Antitumor agents

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KW - Natural products

KW - Total synthesis

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JF - Angewandte Chemie - International Edition

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ER -

A concise synthesis of fumagillol

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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