77 亜鉛アート錯体を用いたPrimary Prostaglandinsの合成(ポスター発表の部)

概要

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A variety of organocuprates occupies a prominent place in the carbon nucleophiles which undergo definite conjugate addition to α,β-unsaturated carbonyl compounds and, hence, are widely used for synthetic purposes. Among many different routs to the Prostaglandins syntheses, the three-component coupling process, i.e., conjugate addition of organocopper reagents to cyclopentenones and alkylation of the resulting enolates (e.g., 1→2→3), is one of the ideal approaches. This approach, however, suffers sometimes a serious drawback of the rapid enolate exchange. In these synthetic studies, we examined (1) proton transfer in the enolate-alkylation stage using (E)-vinylzincate (S)-12, enone (R)-9 and propargylic iodide 13, (2) kinetic resolution during the conjugate addition of (Z)-vinylzincate (±)-19 to the enone (R)-9, where the 4R(C(11) PGs numbering) configuration in 9 serves to control the (R)-chirality at C(15), and (3) enantioface selectivity in the conjugate addition using (Z)-vinylzincate (R)-29, enone 27 and α-side chain 13, where the (15R)-configuration in 29 induces the correct (R)-chirality at C(12).
天然有機化合物討論会の論文
1990-09-25