Studies toward the total synthesis of microsclerodermin G
Date
2010
Authors
Burnett, Cameron Moeller, author
Williams, Robert Michael, advisor
Kennan, Alan J., committee member
Rovis, Tomislav, 1968-, committee member
Bernstein, E. R. (Elliot R.), committee member
Belisle, John Theodore, committee member
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Volume Title
Abstract
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.
Description
Department Head: Ellen R. Fisher.
Rights Access
Subject
synthesis
Macrocyclic compounds -- Synthesis
AMPTD
Peptides -- Synthesis
microsclerodermin G
Amino acids -- Synthesis
organic