title: 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.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, 11510, Puerto Real, Cádiz, Spain. rosario.hernandez@uca.es.
authors.forename: J M
authors.initials: JM
authors.lastname: Botubol-Ares
authors.forename: M J
authors.initials: MJ
authors.lastname: Durán-Peña
authors.forename: A J
authors.initials: AJ
authors.lastname: Macías-Sánchez
authors.forename: J R
authors.initials: JR
authors.lastname: Hanson
authors.forename: I G
authors.initials: IG
authors.lastname: Collado
authors.forename: R
authors.initials: R
authors.lastname: Hernández-Galán
mesh_terms: D001711:Biotransformation; D020171:Botrytis / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D006900:Hydroxylation; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D009154:Mutation; D010100:Oxygen / Q000737:chemistry; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D007783:Lactones; D061065:Polyketides; D010100:Oxygen