Chen, Yuyin, authorWilliams, Robert M., advisor2022-11-282022-11-282006https://hdl.handle.net/10217/235849An asymmetric synthesis of the tetracyclic core of (-)-lemonomycin is presented. It features an efficient route towards a highly versatile tetrahydroisoquinoline intermediate, in which a diastereoselective Pictet-Spengler reaction has been developed. In addition, a novel oxidation was discovered in the process of an azomethine ylide cyclization for construction of C and D rings of lemonomycin. An investigation into the mechanism of this novel oxidation has been carried out and the results discussed. The tetracyclic enamide from this process represents a highly functionalized and versatile intermediate. Interestingly, the enamide double bond proved very resistant to reduction and this transformation was fully investigated. More recently, with high-pressure hydrogenation equipment, promising leads towards hydrogenation of this enamide have been uncovered.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.Asymmetric synthesisAntineoplastic antibioticsText