20 プロスタグランジン類の新合成法

概要

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Newly developed tools for prostaglandin synthesis are described. (1) Transition metal catalyzed reactions of strained oxygen ring systems provide useful methods for site-specific oxygenation of unsaturated carbon skeletons. The reaction pathway of the palladium(0) catalyzed reaction of 1,3-diene 1,2-epoxides is highly dependent on the structure and substitution pattern of the substrates; epoxides derived from flexible dienes isomerize to dienol isomers, whereas cyclic diene epoxides are transformed to β,γ-unsaturated ketones selectively. 1,3-Diene 1,4-epiperoxides give 4-hydroxy-2-alkenones or syn diepoxides depending on the nature of the catalysts. (2) New procedures for vicinal carbon group introduction to α,β-unsaturated ketones have been elaborated on the basis of stoichiometric use of organocopper reagents. Utility of such methodologies is illustrated by the straightforward synthesis of certain prostaglandin derivatives.
天然有機化合物討論会の論文
1980-09-10