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

Sanjay P. Borikar; Vincent Paul; Vedavati G. Puranik; Vilas T. Sathe; Selene Lagunas-Rivera; Mario Ordónez

doi:10.1055/s-0030-1260004

PAPER

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

Sanjay P. Borikar^a, Vincent Paul*^a, Vedavati G. Puranik^a, Vilas T. Sathe^a, Selene Lagunas-Rivera^b, 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

Abstract

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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

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References

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CCDC 813937 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk].