Total synthesis of brevenal; synthesis of the AB- and E- ring subunits of brevenal and studies of olefinic-lactone ring-closing metathesis using a reduced titanium alkylidene; synthesis of (R)-(-)-muscone and (R)-(+)-muscopyridine

This dissertation describes the total synthesis of the marine ladder toxin brevenal utilizing a convergent synthetic strategy. Critical to the success of this work was the use of olefinic-ester cyclization reactions and the utilization of glycal epoxides as precursors to C-C and C-H bonds. Previous total syntheses of brevenal and our strategy for the completion of the molecule are discussed in detail. In addition, olefinic-lactone cyclization reactions that result in the generation of macrocycles are described. The methodology was used to synthesize the natural products muscone and muscopyridine.