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Synthesis of Natural and Unnatural Cyclooligomeric Depsipeptides Enabled by Flow Chemistry
Author(s) -
Lücke Daniel,
Dalton Toryn,
Ley Steven V.,
Wilson Zoe E.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504457
Subject(s) - depsipeptide , chemistry , combinatorial chemistry , nanotechnology , stereochemistry , materials science
Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin ( 1 a ), bassianolide ( 2 b ) and enniatin C ( 1 b ). A reliable flow chemistry protocol was established for the coupling and macrocyclisation to form challenging N‐methylated amides. This flexible approach has allowed the rapid synthesis of both natural and unnatural depsipeptides in high yields, enabling further exploration of their promising biological activity.