Stereoselective synthesis of (-)-spicigerolide.
(-)-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.
Georges
Yohan
Y
Departament de Química Orgánica, Universitat de Barcelona, 08028 Barcelona, Spain.
Ariza
Xavier
X
Garcia
Jordi
J
D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D007783:Lactones; C482142:spicigerolide