Abstract

The synthetic progress towards yaku'amide A is described. The study leads to development of new synthetic methodologies. Base-free regioselective aminohydroxylation is convenient to deliver β-tert-hydroxyamino acids. A sequence consisting of alkylative esterification, Martin sulfurane mediated anti dehydration, a tandem azide reduction-O→N acyl transfer allows the rapid access of E- and Z-dehydroisoleucine-containing peptides from β-tert-hydroxyisoleucine derivatives. Those methods are effective in constructing complicated peptides and advanced subunits of yaku'amide A.

Degree

PhD

College and Department

Physical and Mathematical Sciences; Chemistry and Biochemistry

Rights

http://lib.byu.edu/about/copyright/

Date Submitted

2015-07-01

Document Type

Dissertation

Handle

http://hdl.lib.byu.edu/1877/etd8066

Keywords

yaku'amide A, base-free regioselective aminohydroxylation β-tert-hydroxy amino acids, dehydroamino acids, dehydroisoleucine, Martin sulfurane, anti dehydration, azide reduction, O→N acyl transfer.

Language

english

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