Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1395003 | European Journal of Medicinal Chemistry | 2010 | 9 Pages |
Abstract
We present a simple and general strategy for the synthesis of β,δ-disubstituted-α-methylene-δ-lactones starting from easily available tert-butyl 2-(diethoxyphosphoryl)alk-2-enoates. The elaborated synthetic protocol includes pyrrolidine-catalyzed Michael addition of acetone, diastereoselective reduction of the carbonyl group, lactonization and finally the Horner–Wadsworth–Emmons reaction with formaldehyde. All α-methylene-δ-lactones were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Comparison of cytotoxic activity with corresponding α-methylene-γ-lactones is also discussed.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Łukasz Albrecht, Jakub Wojciechowski, Anna Albrecht, Wojciech M. Wolf, Anna Janecka, Kazimierz Studzian, Urszula Krajewska, Marek Różalski, Tomasz Janecki, Henryk Krawczyk,