title: A stereoselective synthesis of the C9-C19 subunit of (+)-peloruside A.
abstract: The stereoselective synthesis of a C9-C19 fragment of the potent antitumor agent peloruside A is disclosed. The C11 stereogenic centre was created by a vinylogous Mukaiyama aldol reaction following Carreira's protocol, with excellent stereocontrol. The C13 stereogenic centre was introduced by a substrate controlled reduction. The C15 stereocentre was fashioned using Noyori's asymmetric transfer hydrogenation while the Z-trisubstituted double bond was formed by a regioselective hydrostannation of an alkyne followed by methylation of the resultant vinyl stannane using Lipshutz's protocol. The C18 chiral centre was introduced by a chemoenzymatic route.
authors.affiliation: Division of Natural Product Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India. sraghavan@iict.res.in
authors.forename: Sadagopan
authors.initials: S
authors.lastname: Raghavan
authors.forename: V
authors.initials: V
authors.lastname: Vinoth Kumar
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; C414085:peloruside A