Abstract

The title compound was synthesized in 3 steps (regioselective sulfenylation, m-CPBA and Pb(OAc) 4 oxidations) from N-Boc- p-anisidine. Its Diels-Alder reactions with cyclopentadiene took place on the double bonds C 2C 3 or C 5C 6 depending upon the experimental conditions with total endo-selectivity and high π-facial diastereoselectivity. The cycloaddition with trans-piperylene ocurred exclusively on the sulfinylsubstituted dienophilic double bond C 2C 3.

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