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.

The first total synthesis of (-)-pericosine A, methyl (3R,4R,5R,6R)-6-chloro-3,4,5-trihydroxy-1-cyclohex-1-enecarboxylate, from (-)-shikimic acid was accomplished, which led to the revision of the relative configuration and the determination of the absolute configuration of the natural product as 3S,4S,5S,6S.

Carbohydrates U 0500First Total Synthesis of Antitumor Natural Product (+)-and (-)-Pericosine A (I): Determination of Absolute Stereo Structure. -(USAMI*, Y.; TAKAOKA, I.; ICHIKAWA, H.; HORIBE, Y.; TOMIYAMA, S.; OHTSUKA, M.; IMANISHI, Y.; ARIMOTO, M.; J. Org. Chem. 72 (2007) 16, 6127-6134; Osaka Univ. Pharm. Sci., Takatsuki, Osaka 569, Japan; Eng.) -Mischke 52-191

No abstract