title: Enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block.
abstract: A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlighted by the utilization of the palladium-catalyzed enantioselective allylic alkylation of dioxanone substrates to prepare tertiary alcohols.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, USA.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Craig
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Roizen
authors.forename: Russell C
authors.initials: RC
authors.lastname: Smith
authors.forename: Amanda C
authors.initials: AC
authors.lastname: Jones
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D004146:Dioxanes / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D003517:Cyclopentanes; D004146:Dioxanes; D010165:Palladium