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

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 tot...

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Autores principales: Takao, Ken-ichi, Sakamoto, Shu, Touati, Marianne Ayaka, Kusakawa, Yusuke, Tadano, Kin-ichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268616/
https://www.ncbi.nlm.nih.gov/pubmed/23138536
http://dx.doi.org/10.3390/molecules171113330
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author Takao, Ken-ichi
Sakamoto, Shu
Touati, Marianne Ayaka
Kusakawa, Yusuke
Tadano, Kin-ichi
author_facet Takao, Ken-ichi
Sakamoto, Shu
Touati, Marianne Ayaka
Kusakawa, Yusuke
Tadano, Kin-ichi
author_sort Takao, Ken-ichi
collection PubMed
description 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.
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spelling pubmed-62686162018-12-13 Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol Takao, Ken-ichi Sakamoto, Shu Touati, Marianne Ayaka Kusakawa, Yusuke Tadano, Kin-ichi Molecules Article 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. MDPI 2012-11-08 /pmc/articles/PMC6268616/ /pubmed/23138536 http://dx.doi.org/10.3390/molecules171113330 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Takao, Ken-ichi
Sakamoto, Shu
Touati, Marianne Ayaka
Kusakawa, Yusuke
Tadano, Kin-ichi
Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol
title Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol
title_full Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol
title_fullStr Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol
title_full_unstemmed Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol
title_short Asymmetric Construction of All-Carbon Quaternary Stereocenters by Chiral-Auxiliary-Mediated Claisen Rearrangement and Total Synthesis of (+)-Bakuchiol
title_sort asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-bakuchiol
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268616/
https://www.ncbi.nlm.nih.gov/pubmed/23138536
http://dx.doi.org/10.3390/molecules171113330
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