title: Enantioselective total synthesis of (-)-dactylolide.
abstract: [reaction: see text] The enantioselective total synthesis of (-)-dactylolide is reported. The absolute stereochemistry of the tetrahydropyran was established by catalytic asymmetric Jacobsen hetero-Diels-Alder reaction. The remote C19 stereocenter was introduced by a sequence of chelation-controlled Grignard addition and Ireland-Claisen rearrangement.
authors.affiliation: School of Chemistry, F11, The University of Sydney, NSW 2006, Australia.
authors.forename: Ignace
authors.initials: I
authors.lastname: Louis
authors.forename: Natasha L
authors.initials: NL
authors.lastname: Hungerford
authors.forename: Edward J
authors.initials: EJ
authors.lastname: Humphries
authors.forename: Malcolm D
authors.initials: MD
authors.lastname: McLeod
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; C451487:dactylolide