Synthesis of pinguisane-type sesquiterpenoids acutifolone A, pinguisenol, and bisacutifolones by a Diels-Alder dimerization reaction

Junichi Shiina, Masataka Oikawa, Kensuke Nakamura, Rika Obata, Shigeru Nishiyama

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The total synthesis of pinguisane-type sesquiterpenoids, acutifolone A (1) and pinguisenol (2), has been achieved by using the Mukaiyama aldol reaction as the key step. The intermolecular Diels-Alder reaction of these monomelic natural products successfully led to stereoselective dimerization, leading to bisacutifolones A (3) and B (4). Theoretical calculations revealed that the dimerization reaction proceeded through the most stable transition state.

Original languageEnglish
Pages (from-to)5190-5197
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number31
DOIs
Publication statusPublished - 2007 Nov 14

Keywords

  • Autoxidation
  • Biomimetic synthesis
  • Liverwort
  • Terpenoids
  • Total synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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