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 Co 2(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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