Pan, Guojun, authorWilliams, Robert M., advisorHenry, Charles, committee memberMacNeil, Maechael, committee memberRovis, Tomislav, committee memberWood, John L., committee member2007-01-032007-01-032012http://hdl.handle.net/10217/67622The total syntheses of (±)-fawcettimine, (±)-lycoflexine, (±)-fawcettidine, and (±)-lycoposerramine B have been accomplished through an efficient, unified, and stereocontrolled strategy that required sixteen, sixteen, seventeen, and seventeen steps, respectively, from commercially available materials. The key transformations involve: 1) a Diels-Alder reaction between a 1-siloxy diene and an enone to construct the cis-fused 6,5-carbocycles with one all-carbon quaternary center, and 2) a Fukuyama-Mitsunobu reaction to form the azonine ring. Access to the enantioselective syntheses of these alkaloids can be achieved by kinetic resolution of the earliest intermediate via a Sharpless asymmetric dihydroxylation.born digitaldoctoral dissertationsengCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.fawcettiminetotal synthesislycoposerramine BlycoflexinelycopodiumfawcettidineText