Issue 28, 2014

Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones

Abstract

The enantioselective synthesis of (2R,3R,4E,8E)-3-hydroxy-2,4,8-trimethyldeca-4,8-dienolide (5) by ring-closing metathesis is described. This compound is an analogue of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (4) which is a rare 11-membered lactone produced by the fungus, Botrytis cinerea. Mutasynthetic studies with compound 5 using two mutants of B. cinerea led to the isolation of four new highly oxygenated 11-membered lactones (11–14) in which compound 5 has been stereoselectively epoxidized and hydroxylated at sites that were not easily accessible by classical synthetic chemistry.

Graphical abstract: Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones

Supplementary files

Article information

Article type
Paper
Submitted
04 Apr 2014
Accepted
23 May 2014
First published
23 May 2014

Org. Biomol. Chem., 2014,12, 5304-5310

Author version available

Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones

J. M. Botubol-Ares, M. J. Durán-Peña, A. J. Macías-Sánchez, J. R. Hanson, I. G. Collado and R. Hernández-Galán, Org. Biomol. Chem., 2014, 12, 5304 DOI: 10.1039/C4OB00717D

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