Enantioselective total synthesis of (-)-dactylolide.
[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.
Louis
Ignace
I
School of Chemistry, F11, The University of Sydney, NSW 2006, Australia.
Hungerford
Natasha L
NL
Humphries
Edward J
EJ
McLeod
Malcolm D
MD
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; C451487:dactylolide