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

研究成果: Article査読

20 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)5190-5197
ページ数8
ジャーナルEuropean Journal of Organic Chemistry
31
DOI
出版ステータスPublished - 2007 11月 14

ASJC Scopus subject areas

  • 物理化学および理論化学
  • 有機化学

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