Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones
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Author/sBotubol Ares, José Manuel; Durán-Peña, María Jesús; Macías Sánchez, Antonio José; Hanson, J. R.; González Collado, Isidro; Hernández Galán, Rosario
SourceOrganic & Biomolecular Chemistry 2014, 12, 5304
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.