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Synthesis 2007(22): 3512-3518  
DOI: 10.1055/s-2007-990862
PAPER
© Georg Thieme Verlag Stuttgart · New York

First Total Synthesis and Absolute Configuration of the Styryl Lactone Gonioheptolide A

Shuchi Guptaa,1, Murali Rajagopalanb,2, Mamoun M. Alhamadsheha,1, L. M. Viranga Tillekeratnea, Richard A. Hudson*a,b
a Department of Medicinal and Biological Chemistry, College of Pharmacy, University of Toledo, 2801 West Bancroft St., Toledo, OH 43606, USA
b Department of Chemistry, College of Arts and Sciences, University of Toledo, 2801 West Bancroft St., Toledo, OH 43606, USA
Fax: +1(419)5307946; e-Mail: Richard.hudson@utoledo.edu;
Further Information

Publication History

Received 21 April 2007
Publication Date:
29 October 2007 (online)

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Abstract

Efficient asymmetric syntheses of both naturally occurring and non-naturally occurring enantiomers of gonioheptolide A are reported. The absolute configuration of (+)-gonioheptolide A was established by NOESY, Mosher ester analysis, and comparison with the specific rotation of the isolated (+)-gonioheptolide A.

Key words

gonioheptolide A - styryl lactones - natural products - antitumor agents - stereoselective synthesis

1

Current address: Department of Chemistry, Portland State University, Portland, OR, USA.

2

Current address: Schering-Plough Corporation, NJ, USA.