Abstract
A short synthesis of novel prostanoids, 12-epi-carbacyclins 3 and 24, has been accomplished using palladium chemistry as a key step. The silyl enol ether 10a prepared through organopalladium chemistry has been allowed to react with 1-octen-3-one in the presence of <TEX>$Pd(OAc)_2$</TEX> to give compound 12 in a single step. The unusual chemo- and stereoselective reduction of the <TEX>${\alpha},{\beta}$</TEX>-unsaturated ketone in 12 has been effected with (S)-BINALH. Subsequent desilylation and Wittig reaction have provided the Subsequent desilylation and Wittig reaction have provided the <TEX>$PGI_2$</TEX> analogues 3 and 24.
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