Convergent Total Synthesis of Yaku'amide A
| Autor: | Shi Luo, Joseph M. Cardon, Concordia C. L. Lo, Zhiwei Ma, Diego A. Moyá, Yu Cai, Ankur Jalan, Jintao Jiang, Daniel Joaquin, Alexander Ramos, Steven L. Castle |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
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 |
| Zdroj: | Angew Chem Int Ed Engl |
| ISSN: | 1521-3757 0044-8249 |
| DOI: | 10.1002/ange.202014238 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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