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

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

Research output: Contribution to journalArticle

11 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

    Fingerprint

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this