title: Toward the synthesis of (+)-peloruside A via an intramolecular vinylogous aldol reaction.
abstract: The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A is described. The reaction was applied to compound 19 and proceeds in high yield and good levels of diastereoselectivity. Application of the Achmatowicz reaction to this intermediate provided the corresponding pyranone, a late stage intermediate well positioned for conversion to the natural product.
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
authors.forename: Jeffrey A
authors.initials: JA
authors.lastname: Gazaille
authors.forename: Joseph A
authors.initials: JA
authors.lastname: Abramite
authors.forename: Tarek
authors.initials: T
authors.lastname: Sammakia
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; D014753:Vinyl Compounds; C414085:peloruside A; C116609:3-hydroxybutanal