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.
College and Department
Physical and Mathematical Sciences; Chemistry and Biochemistry
BYU ScholarsArchive Citation
Ma, Zhiwei, "Progress Towards the Total Synthesis of Yaku'amide A" (2015). Theses and Dissertations. 6002.
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.