title: Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A.
abstract: Crude Porcine pancreatic lipase was successfully used for the kinetic resolution of axially chiral primary allenic alcohols providing very high enantioselectivities with E values above 200. This simple access to optically active allenes was applied to the total synthesis of the fungal metabolite (-)-striatisporolide A, allowing its unambiguous stereochemical assignment.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
authors.forename: Jan
authors.initials: J
authors.lastname: Deska
authors.forename: Jan-E
authors.initials: JE
authors.lastname: Bäckvall
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000438:Alcohols / Q000737:chemistry / Q000302:isolation & purification*; D000466:Alkadienes / Q000737:chemistry / Q000302:isolation & purification; D000818:Animals; D004951:Esterification; D007166:Immunosuppressive Agents; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D010407:Penicillium / Q000737:chemistry; D013237:Stereoisomerism; D013552:Swine
chemical_list: D000438:Alcohols; D000466:Alkadienes; D007166:Immunosuppressive Agents; C545611:striatisporolide A; C004511:butenolide; D008049:Lipase; D015107:4-Butyrolactone