Valente, Meriah W. N., authorWilliams, Robert M., advisorKurosu, Michio, committee memberKennan, Alan J., committee member2022-11-282022-11-282006https://hdl.handle.net/10217/235848The total synthesis of stephacidin A, avrainvillamide and stephacidin B was envisioned to proceed through a biomimetic intramolecular Diels-Alder cylcoaddition. The Diels-Alder precursor was thought to come from the coupling of (L)-prolinamide with a α-ketoacid indole, which would subsequently form the requisite azadiene. While the desired α-ketoacid indole was not stable enough to be synthetically formed, a pseudo- α-ketoacid was successfully designed. The coupling of this vinyl ether carboxylic acid indole moiety with (L)-prolinamide provides an interesting intramolecular Diels-Alder (IMDA) precursor, which might prove to be a useful synthetic prototype for the IMDA. A similar coupling between a pseudo-α-ketoacid and (L)-prolinamide was applied to a different system of compounds, which led to a biomimetically-inspired intramolecular Diels-Alder reaction that diastereoselectively formed the characteristic bicyclo[2.2.2]diazaoctane core of the brevianamides. A concise synthesis of d,l-brevianamide B was successfully designed through a Fischer indole reaction of the key tricyclic IMDA cycloadduct and phenyl hydrazine. This IMDA / Fischer indole route to form the indolic bicyclo[2.2.2]diazaoctane core has proven to be a versatile method to access C-12a-epi-malbrancheamide and structurally related analogs for biological activity studies.masters thesesengCopyright 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.Indole alkaloids -- SynthesisBiomimeticsText