A divergent synthesis of the delta(13)-9-isofurans.
A stereodivergent total synthesis of the Delta(13)-9-isofurans has been developed. The four core substituted tetrahydrofurans were prepared by the Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation followed by cascade cyclization. The relative configuration at C-8 was inverted by oxidation followed by immediate L-Selectride reduction. The relative configuration of the C-15 diastereomers was assigned by (S)-Binol/LAH/EtOH reduction of the corresponding enone. This synthesis of the Delta(13)-9-isofurans will provide sufficient material for further investigation of their biological activity.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Gu
Peiming
P
Li
Rui
R
D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D005663:Furans; C018674:tetrahydrofuran