Issue 28, 2014
From the journal:

Organic & Biomolecular Chemistry

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

J. M. Botubol-Ares,a   M. J. Durán-Peña,a   A. J. Macías-Sánchez,a   J. R. Hanson,b   I. G. Colladoa  and  R. Hernández-Galán*a  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Puerto Real, Cádiz, Spain
E-mail: rosario.hernandez@uca.es

b Department of Chemistry, University of Sussex, Brighton, Sussex, UK
E-mail: j.r.hanson@sussex.ac.uk

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

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Article information

DOI
https://doi.org/10.1039/C4OB00717D
Article type
Paper
Submitted
04 Apr 2014
Accepted
23 May 2014
First published
23 May 2014

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

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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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