Stereoselective synthesis of bicyclic lactones by annelation with functionalized orthoesters.
An efficient two-step annelation of functionalized orthoesters with trimethylsilyloxyfuran derivatives, which delivers suitably decorated bicyclo[3.n.0]lactones in high overall yields and with complete diastereocontrol of up to three contiguous stereocenters, is reported.
Maulide
Nuno
N
Université Catholique de Louvain, Département de Chimie, 1 Place Louis Pasteur, B-1348 Louvain-la-Neuve, Belgium.
Markó
István E
IE
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D005663:Furans / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D001643:Bridged Bicyclo Compounds; D004952:Esters; D005663:Furans; D007783:Lactones; D014297:Trimethylsilyl Compounds