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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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