Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-epi-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (-)-Etharvensin

Prasad, Kavirayani R and Gholap, Shivajirao L (2008) Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-epi-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (-)-Etharvensin. In: Journal of Organic Chemistry, 73 (1). pp. 2-11.

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Abstract

Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from D-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of \gamma-phenyl-\gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	Copyright of this article belongs to American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	06 Aug 2008
Last Modified:	19 Sep 2010 04:48
URI:	http://eprints.iisc.ac.in/id/eprint/15484

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