Jia, Xiangna, authorWilliams, Robert M., advisor2022-11-282022-11-282009https://hdl.handle.net/10217/235857Presented herein is a twenty-five linear step synthetic progress toward an asymmetric total synthesis of the Stemona alkaloid tuberostemoninol. A diastereoselective intramolecular Pauson-Khand reaction of a glycinate derivative served to construct the BC ring system and set one of the two quaternary carbon centers present in the target molecule in high yield. The γ-lactone E ring and azepine D ring were constructed subsequently. Several approaches were explored for the introduction of the γ-lactone E ring carbon skeleton containing the α-methylene group. Further elaboration of the BCDE tetracycle toward tuberostemoninol was performed to afford the corresponding ketone compound, which makes completion of the total synthesis possible in ten steps.doctoral 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.Alkaloids -- SynthesisOrganic compounds -- SynthesisText