Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A.
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.
Deska
Jan
J
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
Bäckvall
Jan-E
JE
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
D000438:Alcohols; D000466:Alkadienes; D007166:Immunosuppressive Agents; C545611:striatisporolide A; C004511:butenolide; D008049:Lipase; D015107:4-Butyrolactone