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Total Synthesis of Halipeptin A: A Potent Antiinflammatory Cyclic Depsipeptide
Author(s) -
Yu Shouyun,
Pan Xianhua,
Lin Xianfeng,
Ma Dawei
Publication year - 2004
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.200461239
Subject(s) - depsipeptide , total synthesis , natural product , enantioselective synthesis , stereochemistry , chemistry , aldol reaction , claisen rearrangement , stereocenter , organic chemistry , catalysis
The antiinflammatory drug halipeptin A ( 1 ) is a 17‐membered cyclic depsipeptide made up of L ‐alanine, α‐methylcysteine, decanoic acid, and isoleucine residues. Key steps in its total synthesis, which helped to confirm the stereochemistry of the natural product, include a borane‐mediated aldol reaction and an asymmetric aza‐Claisen rearrangement.