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

Shuchi Gupta; Murali Rajagopalan; Mamoun M. Alhamadsheh; L. M. Viranga Tillekeratne; Richard A. Hudson

doi:10.1055/s-2007-990862

PAPER

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

Shuchi Gupta^a,1, Murali Rajagopalan^b,2, Mamoun M. Alhamadsheh^a,1, L. M. Viranga Tillekeratne^a, 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;

Abstract

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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

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References

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

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

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