SUMMARYStarting from an easily obtainable and already described intermediate 2, the total synthesis of three pseudoguaianolides is described. The transformation involves functionalization of the cyclopentane ring.Recently several synthetic efforts have aimed at the total synthesis of sesquiterpene lactones of the pseudoguaianolide family . Our general approach towards this class of compounds centers about the dione 1 which we prepared in a five step sequence from 2-methyl-2-cyclopentenone in 61 % overall yield . The synthetic potentiality of this synthon has already been demonstrated by its transformation into the y-lactone 2 during our total synthesis of (+) -damsinlc.We now want to report synthetic transformations in the cyclopentane moiety with emphasis on the introduction of a double bond and of an angular hydroxyl group (C-1). The investigations led to the first total synthesis of the title compounds, three members of this large family.
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