Nazarov cyclization entry to chiral bicyclo[5.3.0]decanoid building blocks and its application to formal synthesis of (-)-englerin A

Keisuke Morisaki, Yusuke Sasano, Takahiro Koseki, Takuro Shibuta, Naoki Kanoh, Wen Hua Chiou, Yoshiharu Iwabuchi

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A divergent entry to the chiral bicyclo[5.3.0]-decane skeletons relevant to sesqui- and higher terpenoids has been achieved. Its usefulness was demonstrated by formal synthesis of a guaiane sesquiterpenoid (-)-englerin A. The key reactions are (i) diastereoselective Nazarov cyclization for stereoselective construction of the bicyclo[5.3.0]decane skeleton, (ii) intramolecular C-H amination for tuning an oxidation state, and (iii) introduction of an alkyl group to a β-alkoxy ketone with a zinc(II) ate complex.

Original languageEnglish
Pages (from-to)5142-5145
Number of pages4
JournalOrganic letters
Volume19
Issue number19
DOIs
Publication statusPublished - 2017 Jan 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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