1. Convergent Total Synthesis of Yaku'amide A.
- Author
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Cai, Yu, Ma, Zhiwei, Jiang, Jintao, Lo, Concordia C. L., Luo, Shi, Jalan, Ankur, Cardon, Joseph M., Ramos, Alexander, Moyá, Diego A., Joaquin, Daniel, and Castle, Steven L.
- Subjects
NATURAL products ,PEPTIDE synthesis ,AMINO acids ,ISOMERIZATION - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2021
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