Studies on Highly Stereoselective Synthetic Process Based on Palladium-Catalyzed Reactions for Biologically Active Compounds

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1. We developed general synthetic methods for <alpha> -methylene ketones and lactones, important functional group for biologically activity, by the palladium-catalyzed decarboxylation-deacetoxylation of allyl acetoxymethyl- <beta> -keto carboxylates. We also found several palladium-catalyzed reactions of propargyl compounds.2. Optically active hydroindenone was synthesized as a precusor of vitamin <D_3> by palladium-catalyzed syn- <S_N> 2' cyclization of [Z,Z(22S,23R)]-ene oxide, prepared by Sharpless epoxidation. The formal butenylation was also carried out by palladium catalyzed allylation, followed by hydrogenolysis with formate.3. Efficient chirality transfer was observed in the palladium-catalyzed cyclization of the methyl (3R)-methoxycarbonyloxy-(4E)-decenyl malonate and its (Z)-isomer to the (3R)-alkyl- <delta> -lactone and (3S)-lactone respectively.