Enantioselective synthesis of rumphellaone A via epoxy nitrile cyclization

Takafumi Hirokawa, Tomohiro Nagasawa, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The first enantioselective synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane derivative incorporating a γ-lactone ring as its structural feature, has been achieved by using base-induced intramolecular cyclization of an epoxy nitrile intermediate to install its cyclobutane skeleton as well as three contiguous stereocenters as the key transformation.

Original languageEnglish
Pages (from-to)705-706
Number of pages2
JournalTetrahedron Letters
Volume53
Issue number6
DOIs
Publication statusPublished - 2012 Feb 8

Keywords

  • Caryophyllane
  • Cytotoxic
  • Epoxy nitrile cyclization
  • Rumphellaone A

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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