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Synthesis of Natural and Unnatural Cyclooligomeric Depsipeptides Enabled by Flow Chemistry.

ABSTRACT: 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.

SUBMITTER: Lucke D

PROVIDER: S-EPMC4797712 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Synthesis of Natural and Unnatural Cyclooligomeric Depsipeptides Enabled by Flow Chemistry.

Lücke Daniel D Dalton Toryn T Ley Steven V SV Wilson Zoe E ZE

Chemistry (Weinheim an der Bergstrasse, Germany) 20160204 12

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 explo ...[more]

PMID: 26844421

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