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July 12, 2007The Journal of Organic Chemistry

First Total Synthesis of Antitumor Natural Product (+)- and (−)-Pericosine A: Determination of Absolute Stereo Structure†

Yoshihide Usami Isao Takaoka Hayato Ichikawa Yusuke Horibe Syunsuke Tomiyama Misako Ohtsuka Yumi Imanishi Masao Arimoto

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Abstract

The first total synthesis of (+)- and (-)-pericosine A has been achieved, enabling the revision and determination of the absolute configuration of this antitumor natural product as methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate. Every step of this total synthesis proceeded well with excellent stereoselectivity. Structures of the intermediates in crucial steps were confirmed by detailed 2D NMR analysis.

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Usami et al. (2007) studied this question.

synapsesocial.com/papers/6a98ccb055be1aa440bd4239 https://doi.org/10.1021/jo070715l

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