Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol

Ken Ichi Takao, Sakamoto Shu, Marianne Ayaka Touati, Yusuke Kusakawa, Kin Ichi Tadano

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

An asymmetric Claisen rearrangement using Oppolzer's camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.

Original languageEnglish
Pages (from-to)13330-13344
Number of pages15
JournalMolecules
Volume17
Issue number11
DOIs
Publication statusPublished - 2012 Nov

Keywords

  • Camphorsultam
  • Chiral auxiliary
  • Claisen rearrangement
  • Quaternary stereocenter
  • Total synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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