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Issue 28, 2014
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Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones

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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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Publication details

The article was received on 04 Apr 2014, accepted on 23 May 2014 and first published on 23 May 2014


Article type: Paper
DOI: 10.1039/C4OB00717D
Citation: 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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