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

Fingerprint

Dimerization
dimerization
Diels-Alder reactions
synthesis
Biological Products
products
pinguisenol
3-hydroxybutanal

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of pinguisane-type sesquiterpenoids acutifolone A, pinguisenol, and bisacutifolones by a Diels-Alder dimerization reaction. / Shiina, Junichi; Oikawa, Masataka; Nakamura, Kensuke; Obata, Rika; Nishiyama, Shigeru.

In: European Journal of Organic Chemistry, No. 31, 2007, p. 5190-5197.

Research output: Contribution to journalArticle

Shiina, Junichi ; Oikawa, Masataka ; Nakamura, Kensuke ; Obata, Rika ; Nishiyama, Shigeru. / Synthesis of pinguisane-type sesquiterpenoids acutifolone A, pinguisenol, and bisacutifolones by a Diels-Alder dimerization reaction. In: European Journal of Organic Chemistry. 2007 ; No. 31. pp. 5190-5197.
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AU - Nishiyama, Shigeru

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