A Concise Synthesis of Fumagillol

✍ Scribed by David A. Vosburg; Sven Weiler; Erik J. Sorensen

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 100 KB
• Volume: 38
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/(sici)1521-3773(19990401)38:7<971::aid-anie971>3.0.co;2-w

✦ Synopsis

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.