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Molecules 2012, 17(11), 13330-13344; doi:10.3390/molecules171113330
Article

Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol

* , , ,  and *
Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
* Authors to whom correspondence should be addressed.
Received: 9 October 2012 / Revised: 23 October 2012 / Accepted: 2 November 2012 / Published: 8 November 2012
(This article belongs to the Special Issue Claisen Rearrangement)
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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: Claisen rearrangement; chiral auxiliary; camphorsultam; quaternary stereocenter; total synthesis Claisen rearrangement; chiral auxiliary; camphorsultam; quaternary stereocenter; total synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Takao, K.-I.; Sakamoto, S.; Touati, M.A.; Kusakawa, Y.; Tadano, K.-I. Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol. Molecules 2012, 17, 13330-13344.

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