EFFICIENT SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS EMPLOYING PALLADIUM-CATALYZED CYCLOALKENYLATION AS A KEY STEP

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The aim of this research is to investigate total syntheses of bioactive natural products, such as quadron and C_<20> gibberellins, employing the palladium-catalyzed cycloalkenylaton developed by the author as a key step.(1) Synthetic Studies on Antitumor agent Quadrone SynthesisThe author has succeeded in synthesizing the basic carbon skeleton of quadrone using the palladium-catalyzed cyclolakenylation of the cross conjugated silyl enol ether possessing an allyl group at one of the angular position of the trans-hydrindane.(2) Synthetic Studies on Plant Regulator Hormone C_<20> Gibberellin SynthesisFirst of all, the CD ring system, bycyclo [3.2.1] octane, was constructed using the palladium-catalyzed cycloalkenylation as the first key steps. After introduction of the diene and dienophile parts on the bicyclo [3.2.1]-octane ring compound, the intramolecular Diels-Alder reaction of it was performed to give rise to the desired penta cyclic compound as a single stereoisomer. Functional group manipulation of the cyclization product furnished(-)-GA_<112>.