Jiménez-Somarribas, Alberto, authorWilliams, Robert M., advisorWood, John L., committee memberShi, Yian, committee memberLadanyi, Branka M., committee memberCrick, Dean C., committee member2007-01-032007-01-032013http://hdl.handle.net/10217/80986Documented herein are efforts towards the asymmetric total synthesis of (-)-lemonomycin, a member of the tetrahydroisoquinoline antitumor antibiotics family of natural products. We describe a concise route for the assembly of the tetracyclic core of this molecule, which involves a Pictet-Spengler reaction for the construction of the tetrahydroisoquinoline fragment and an azomethine ylide [3+2] dipolar cycloaddition for the construction of the diazabicyclo[3.2.1]octane ring system. The above-described synthetic efforts, while not totally successful, provide the basis for the future completion of the total synthesis of this natural product and other related compounds.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.[3+2] dipolar cycloadditionPictet-Spengler reactionLemonomycinasymmetric synthesisText