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First total synthesis of antitumor natural product (+)- and (-)-pericosine A: determination of absolute stereo structure
Authors:Usami Yoshihide  Takaoka Isao  Ichikawa Hayato  Horibe Yusuke  Tomiyama Syunsuke  Ohtsuka Misako  Imanishi Yumi  Arimoto Masao
Institution:Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp
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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