Usami Yoshihide, Takaoka Isao, Ichikawa Hayato, Horibe Yusuke, Tomiyama Syunsuke, Ohtsuka Misako, Imanishi Yumi, Arimoto Masao
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
J Org Chem. 2007 Aug 3;72(16):6127-34. doi: 10.1021/jo070715l. Epub 2007 Jul 12.
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.
(+)-和(-)-佩里可辛A的首次全合成已经实现,从而能够修正和确定这种抗肿瘤天然产物的绝对构型为甲基(3S,4S,5S,6S)-6-氯-3,4,5-三羟基-1-环己烯-1-羧酸盐。该全合成的每一步都进展顺利,具有出色的立体选择性。关键步骤中间体的结构通过详细的二维核磁共振分析得以确证。