title: Synthesis of the Prelog-Djerassi lactone via an asymmetric hydroformylation/crotylation tandem sequence.
abstract: A synthesis of the Prelog-Djerassi lactone [(+)-1] has been accomplished in three isolations and 57% overall yield from the known vinyl ortho ester 2. A Rh(I)-catalyzed asymmetric hydroformylation/crotylation tandem sequence has been developed and used to set the C2-C4 stereochemistry. A Rh(I)-catalyzed asymmetric hydrogenation was employed to set the C6 sterechemistry, resulting in an unusually short and efficient enantioselective synthesis of this touchstone molecule from achiral starting material.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706-1322, United States.
authors.forename: Roberto M
authors.initials: RM
authors.lastname: Risi
authors.forename: Steven D
authors.initials: SD
authors.lastname: Burke
mesh_terms: D002384:Catalysis; D004952:Esters; D006865:Hydrogenation; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007783:Lactones; D012238:Rhodium