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Chemistry. 2016 Mar 14;22(12):4206-17. doi: 10.1002/chem.201504457. Epub 2016 Feb 4.

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

Author information

1
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
2
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK. zw261@cam.ac.uk.

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.

KEYWORDS:

cyclooligomeric depsipeptides; flow chemistry; macrocycles; natural products; peptides

PMID:
26844421
PMCID:
PMC4797712
DOI:
10.1002/chem.201504457
[Indexed for MEDLINE]
Free PMC Article

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