Synthesis of aspergillide A from a synthetic intermediate of aspergillide B

Tomohiro Nagasawa, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

The first synthesis of aspergillide A, a cytotoxin produced by a marine-derived fungus, has been achieved from a synthetic intermediate of aspergillide B by using a proline-mediated epimerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis-isomer via a retro-oxy-Michael/oxy-Michael sequence as the key transformation.

Original languageEnglish
Pages (from-to)875-877
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number5
DOIs
Publication statusPublished - 2010 Feb 3

Keywords

  • Aspergillide
  • Cytotoxic
  • Epimerization
  • Macrolide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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