Tetrahedron Letters p. 3187 - 3190 (1996)
Update date:2022-08-03
Topics:
Bartolome, Jose M.
Carreno, M. Carmen
Urbano, Antonio
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 C2-C3 or C5-C6 depending upon the experimental conditions with total endo-selectivity and high π-facial diastereoselectivity. The cycloaddition with trans-piperylene occurred exclusively on the sulfinylsubstituted dienophilic double bond C2-C3.
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