Studies toward the total synthesis of vinigrol

Abstract

This thesis presents the work done toward the total synthesis of vinigrol. The studies described here are divided into three main approaches. First, the oxy-Cope/Claisen/ene and the oxy-Cope/ene reactions have been developed to provide cis-decalin systems. These methodologies have been applied for the synthesis of the core of vinigrol. Second, a synthetic route that includes the exploitation of the hydroxy-directed Diels-Alder reaction to construct the vinigrol cis-decalin was developed. Two different strategies were developed to close the remaining eight-membered ring: a ring closing metathesis and a Claisen rearrangement. Finally, the sequential hydroxy-directed Diels-Alder/Claisen reaction was adapted for the synthesis of the six- and eight-membered rings of vinigrol.