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

doi:10.3390/molecules171113330

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

Department of Applied Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	13330-13344
Number of pages	15
Journal	Molecules
Volume	17
Issue number	11
DOIs	https://doi.org/10.3390/molecules171113330
Publication status	Published - 2012 Nov

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Keywords

Camphorsultam
Chiral auxiliary
Claisen rearrangement
Quaternary stereocenter
Total synthesis

ASJC Scopus subject areas

Organic Chemistry
Medicine(all)

Cite this

Takao, K., Shu, S., Touati, M. A., Kusakawa, Y., & Tadano, K. I. (2012). Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol. Molecules, 17(11), 13330-13344. https://doi.org/10.3390/molecules171113330

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Access to Document

10.3390/molecules171113330