A short entry to alpha-substituted gamma-alkylidene pentenolides. Synthesis and preliminary biological evaluation of novel gelastatin analogues.

J Org Chem

Centre for New Antivirals and Antineoplastics, Department of Inorganic and Organic Chemistry, Charles University, Faculty of Pharmacy, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic.

Published: January 2009

Biologically interesting 2-substituted 4-alkylidene pentenolides were prepared with complete control of regio- and stereoselectivity from 2-iodo allylic alcohols via an array of Pd-catalyzed processes, including alkynylation with methyl propiolate, tributyltin hydride addition, and alpha-functionalization. Some of the compounds possess selective cytostatic activity against ovarian carcinoma HeLa S3 and leukemia CCRF-CEM cell lines.

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http://dx.doi.org/10.1021/jo802082tDOI Listing

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