A concise synthesis of fumagillol

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

Research output: Contribution to journalArticle

39 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 languageEnglish (US)
Pages (from-to)971-974
Number of pages4
JournalAngewandte Chemie - International Edition
Volume38
Issue number7
DOIs
StatePublished - Apr 1 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • Angiogenesis
  • Antitumor agents
  • Fumagillin
  • Natural products
  • Total synthesis

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