Burnett, Cameron Moeller, authorWilliams, Robert Michael, advisorKennan, Alan J., committee memberRovis, Tomislav, 1968-, committee memberBernstein, E. R. (Elliot R.), committee memberBelisle, John Theodore, committee member2007-01-032007-01-032010http://hdl.handle.net/10217/39035Department Head: Ellen R. Fisher.We report our studies toward the synthesis of microsclerodermin G, a cyclic hexapeptide with antifungal and antitumor activity. The dehydrotryptophan amino acid was synthesized according to literature precedents. (3R)-γ-amino-β-hydroxybutyric acid (GABOB) was synthesized according to previous methodology from our research group. An aspartate-based precursor to the pyrrolidinone moiety of microsclerodermin G was prepared in four steps from known materials. 3-amino-6-methyl-12-phenyl-2,4,5-trihydroxydodeca-7,9,11-trienoic acid (AMPTD) was prepared in seven steps from known materials; the synthesis utilized Evans' chiral oxazolidinone glycolate aldol reaction and the sulfinimine-based Mannich reaction developed by Ellman. Syntheses of two dipeptides are reported, as are other attempts at coupling of the various amino acids.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.synthesisAMPTDmicrosclerodermin GorganicMacrocyclic compounds -- SynthesisPeptides -- SynthesisAmino acids -- SynthesisText