4.7 Article

A Short Entry to α-Substituted γ-Alkylidene Pentenolides. Synthesis and Preliminary Biological Evaluation of Novel Gelastatin Analogues

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 2, Pages 703-709

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo802082t

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Funding

  1. Ministry of Education, Youth and Sports of the Czech Republic [1M0508, MSM002162089-2]
  2. Czech Science Foundation [203/07/1302]

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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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