Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter

Ryo Towada, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The first total synthesis of the marine-derived cytotoxin topsentolide A2, which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C2, from a synthetic intermediate of topsentolide A2 was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide A2 with HCl/MeOH brought about its quantitative conversion into topsentolide C2.

Original languageEnglish
Pages (from-to)3774-3781
Number of pages8
JournalTetrahedron
Volume70
Issue number24
DOIs
Publication statusPublished - 2014 Jun 17

Keywords

  • Artifact
  • Cytotoxic
  • Marine natural product
  • Oxylipin
  • Topsentolide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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