Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran

Tomohiro Nagasawa, Tomoo Nukada, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2- acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps.

Original languageEnglish
Pages (from-to)2882-2888
Number of pages7
JournalTetrahedron
Volume67
Issue number16
DOIs
Publication statusPublished - 2011 Apr 22

Keywords

  • Aspergillide
  • Cytotoxic
  • Isomerization
  • Macrolide
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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