Abstract
Abstract A substituted penthynylcyclopentene precursor for the synthesis of pentalenic acid by intramolecular Pauson–Khand cycloaddition reaction has been prepared in high yield. Reaction with Co2(CO)8 produces triquinane econes in an overall yield of 33%. Three of the four possible stereoisomeric products are formed, with two of them, making up ca. 80% of the product mixture, possessing the necessary exo-methyl stereochemistry at C-9 for further elaboration into pentalenic acid. A formal synthesis of the latter was completed by reduction of one of the enone isomers into a ketone which had previously been carried on to the natural product.
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