Enantioselective synthesis and biological activity of (3S,4R)- and (3S,4S)-3-hydroxy-4-hydroxymethyl-4-butanolides in relation to PGE(2)

Abstract

Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [3H]-PGE2 binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE 2. Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.