Concise enantio- and diastereoselective total syntheses of fumagillol, RK-805, FR65814, ovalicin, and 5-demethylovalicin

Junichiro Yamaguchi, Maya Toyoshima, Mitsuru Shoji, Hideaki Kakeya, Hiroyuki Osada, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

(Chemical Equation Presented) L-Proline-mediated α-aminoxylation is a key step in the enantio- and diastereoselective total syntheses of fumagillin, ovalicin, and related compounds (see scheme). These compounds contain a cyclohexane ring, two epoxides, and five or six contiguous stereogenic centers, and they display anti-angiogenesis or immunosuppressive properties.

Original languageEnglish
Pages (from-to)789-793
Number of pages5
JournalAngewandte Chemie - International Edition
Volume45
Issue number5
DOIs
Publication statusPublished - 2006 Jan 23

Keywords

  • Asymmetric synthesis
  • Inhibitors
  • Natural products
  • Organocatalysis
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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