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

doi:10.3390/molecules171113330

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

Department of Applied Chemistry

Research output: Contribution to journal › Article

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 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

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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10.3390/molecules171113330

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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.",

keywords = "Camphorsultam, Chiral auxiliary, Claisen rearrangement, Quaternary stereocenter, Total synthesis",

author = "Takao, {Ken Ichi} and Sakamoto Shu and Touati, {Marianne Ayaka} and Yusuke Kusakawa and Tadano, {Kin Ichi}",

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T1 - Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol

AU - Takao, Ken Ichi

AU - Shu, Sakamoto

AU - Touati, Marianne Ayaka

AU - Kusakawa, Yusuke

AU - Tadano, Kin Ichi

PY - 2012/11

Y1 - 2012/11

N2 - 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.

AB - 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.

KW - Camphorsultam

KW - Chiral auxiliary

KW - Claisen rearrangement

KW - Quaternary stereocenter

KW - Total synthesis

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