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2967704 
Journal Article 
Synthesis and cytotoxic evaluation of beta-alkyl or beta-aryl-delta-methyl-alpha-methylene-delta-lactones. Comparison with the corresponding gamma-lactones 
Albrecht, L; Wojciechowski, J; Albrecht, A; Wolf, WM; Janecka, A; Studzian, K; Krajewska, U; Rózalski, M; Janecki, T; Krawczyk, H 
2010 
Yes 
European Journal of Medicinal Chemistry
ISSN: 0223-5234
EISSN: 1768-3254 
45 
2 
710-718 
English 
19962797 
We present a simple and general strategy for the synthesis of beta,delta-disubstituted-alpha-methylene-delta-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 alpha-methylene-delta-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 alpha-methylene-gamma-lactones is also discussed.