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Convergent Total Synthesis of Yaku'amide A
Author(s) -
Cai Yu,
Ma Zhiwei,
Jiang Jintao,
Lo Concordia C. L.,
Luo Shi,
Jalan Ankur,
Cardon Joseph M.,
Ramos Alexander,
Moyá Diego A.,
Joaquin Daniel,
Castle Steven L.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202014238
Subject(s) - regioselectivity , chemistry , azide , isomerization , amide , alkene , reagent , stereospecificity , total synthesis , natural product , organic chemistry , combinatorial chemistry , stereochemistry , catalysis
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.