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Synthesis 2008(21): 3465-3472
DOI: 10.1055/s-0028-1083181
DOI: 10.1055/s-0028-1083181
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkExtension of the Library of Biologically Active γ-Alkylidene Butenolides
Further Information
Received
23 June 2008
Publication Date:
16 October 2008 (online)
Publication History
Publication Date:
16 October 2008 (online)

Abstract
γ-Alkylidene butenolides bearing a deoxyriboside, a steroid, and a metallocene moiety were synthesized by stereoselective sequential cross-coupling lactonization procedure from the corresponding functionalized terminal alkynes with 3-iodopropenoic acids. The high selectivity of the butenolide ring formation was secured by the Pd/Cu salt ratio. The resulting compounds were tested for antifungal and cytostatic properties. Most notably, γ-alkylidene butenolides bearing deoxyriboside moiety showed promising cytostatic activity in the micromolar range.
Key words
cross-coupling - lactones - catalysis - antitumor agents - palladium
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