| 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. |
