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Synthesis 2011(10): 1595-1598  
DOI: 10.1055/s-0030-1260004
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

First Total Synthesis of 5-Hydroxy-3-methyl-4-propylsulfanyl-5H-furan-2-one: A Cancer Chemopreventive Agent

Sanjay P. Borikara, Vincent Paul*a, Vedavati G. Puranika, Vilas T. Sathea, Selene Lagunas-Riverab, Mario Ordónez*b
a Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India
Fax: +91(20)25902629; e-Mail: vp.swamy@ncl.res.in; e-Mail: palacios@ciq.uaem.mx;
b Centro de Investigaciones Quimicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Morelos, México
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Publication History

Received 2 March 2011
Publication Date:
15 April 2011 (online)

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Abstract

The first total synthesis of 5-hydroxy-3-methyl-4-propylsulfanyl-5H-furan-2-one, a newly discovered natural product with anticancer property is described by two different routes. A sequence involving an incorporation of a methyl group via a Gilman reagent and a chemoselective reduction of a cyclic anhydride functionality are the key steps. The methods proposed start from easily available starting materials and allow ready preparation of the final compound in good overall yield.

Key words

Allium cepa - synthesis - Gilman reagent - chemopreventive - selective