Synthesis 2007(20): 3219-3225  
DOI: 10.1055/s-2007-990798
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Syntheses of Diastereomers of Antitumor Natural Product Pericosine A from (-)-Quinic Acid

Yoshihide Usami*, Yasuko Ueda
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan
Fax: +81(726)901005; e-Mail: usami@gly.oups.ac.jp;
Further Information

Publication History

Received 18 May 2007
Publication Date:
21 September 2007 (online)

Abstract

The stereoselective syntheses of diastereomers of antitumor natural pericosine A from (-)-quinic acid were achieved. One of the diastereomers, methyl (3R,4S,5S,6R)-6-chloro-3,4,5-trihydroxycyclohex-1-enecarboxylate, possesses the reported structure of pericosine A. The reported relative configuration of natural pericosine A was shown to be incorrect.