title: Stereoselective synthesis of (-)-spicigerolide.
abstract: (-)-Spicigerolide was stereoselectively synthesized from a protected (S)-lactaldehyde. The synthesis of the polyacetylated framework relied on two Zn-mediated stereoselective additions of alkynes to aldehydes as well as a regiocontrolled [3,3]-sigmatropic rearrangement of an allylic acetate. The pyranone moiety was constructed via ring-closing metathesis.
authors.affiliation: Departament de Química Orgánica, Universitat de Barcelona, 08028 Barcelona, Spain.
authors.forename: Yohan
authors.initials: Y
authors.lastname: Georges
authors.forename: Xavier
authors.initials: X
authors.lastname: Ariza
authors.forename: Jordi
authors.initials: J
authors.lastname: Garcia
mesh_terms: D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D007783:Lactones; C482142:spicigerolide