I. Total synthesis of trichoaurantianolide C and D II. Studies toward the total synthesis of norzoanthamine

I. The total synthesis of the trichoaurantianolide C and D has been accomplished. Previous studies established an enantiocontrolled route to the common 5-7-5 core of the natural products. Due to the numerous difficulties encountered in late stage synthetic manipulations, several end game strategies were explored. Ultimately, a diastereoselective addition of the TMEDA complex of isopropenyl lithium and subsequent allylic C-H oxidation were utilized to complete the necessary functionalization. The enantiocontrolled route provided optically enriched material which confirmed the absolute configuration of the trichoaurantianolides.;II. An enantiocontrolled route to the functionalized ABC ring system of norzoanthamine has been developed. A diastereoselective Ireland-Claisen rearrangement was utilized to install the adjacent C12 and C21 stereocenters. The AB ring system was completed by an endo selective intramolecular Diels-Alder reaction featuring a nitro-activated dienophile. A PCC mediated tandem oxidation-Prins cyclization was explored for C ring cyclization, but was hampered by low yields. An alternate C ring cyclization utilizing ring closing metathesis was developed.