1. Convergent Total Synthesis of Yaku'amide A
- Author
-
Shi Luo, Joseph M. Cardon, Concordia C. L. Lo, Zhiwei Ma, Diego A. Moyá, Yu Cai, Ankur Jalan, Jintao Jiang, Daniel Joaquin, Alexander Ramos, and Steven L. Castle
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Alkene ,Regioselectivity ,Total synthesis ,Antineoplastic Agents ,Stereoisomerism ,General Chemistry ,General Medicine ,010402 general chemistry ,Hydroxylation ,01 natural sciences ,Combinatorial chemistry ,Catalysis ,Article ,0104 chemical sciences ,chemistry.chemical_compound ,Stereospecificity ,chemistry ,Amide ,Reagent ,Azide ,Isomerization ,Oligopeptides - Abstract
Total synthesis of the anticancer peptide natural product yaku'amide A is reported. Its β-tert-hydroxy amino acids were prepared by regioselective aminohydroxylation involving a chiral mesyloxycarbamate reagent. Stereospecific construction of the E- and Z-ΔIle residues was accomplished through a one-pot reaction featuring anti dehydration, azide reduction, and O→N acyl transfer. Alkene isomerization was negligible during this process. These methods enabled a highly convergent and efficient synthetic route to the natural product.
- Published
- 2021