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

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2014Department
Química OrgánicaSource
Organic & Biomolecular Chemistry 2014, 12, 5304Abstract
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.
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