Regiospecific synthesis of polysubstituted furans and their application in organic synthesis

Abstract

The role played by 3,4-bis(trimethylsilyl)furan, 2,4-bis(trimethylsilyl)furan and 3,4-bis(tri-n-butylstannyl)furan as building blocks in the preparation of 2,3-disubstituted furans, 3,4-disubstituted furans, as well as 2,3,5-trisubstituted furans will be summarized. The synthetic potential of furan and its polysubstituted derivatives will be illustrated by our Diels-Alder reaction - deoxygenation route for the realization of several theoretically interesting benzenoid molecules, as well as by the preparation of 2-butenolides which are precursors of the naturally occurring prehispanolone, sphydrofuran and secosyrins.