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Abstract by Yu Cai

Personal Infomation


Presenter's Name

Yu Cai

Degree Level

Doctorate

Abstract Infomation


Department

Chemistry and Biochemistry

Faculty Advisor

Steven Castle

Title

Progress towards the total synthesis of Yaku\'amide A

Abstract

The synthetic progress towards yaku’amide A, which is a natural medium-sized peptide with potent anticancer acitivties and unique mode of action, will be described. New synthetic methodologies were developed in the course of the study. Base-free regioselective aminohydroxylation is effective to deliver β-tert- hydroxyamino acids. A sequence consisting of alkylative esterification, Martin sulfurane mediated anti dehydration, and a tandem azide reduction–O→N acyl transfer allows rapid access to E- and Z-dehydroisoleucine-containing peptides from β-tert-hydroxyisoleucine derivatives. These methods should also be applicable to the construction of other complicated natural peptides. The synthesis of yaku'amide A should be completed soon based on our developed synthetic methods.