T. Ganesh, K. Sharma, G. Krupadanam
Dec 1, 2001
Citations
0
Influential Citations
5
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
A novel regioselective synthesis of neolignan, 6-(3-hydroxy-1-propenyl)-2-phenyl-2,3-dihydrobenzo[b]-1,4-dioxin-3-methanol, is described. 2-[bromo(phenyl)methyl]-oxirane upon condensation with 3,4-dihydroxybenzaldehyde gave regioselectively (±)-trans-3-hydroxymethyl-2-phenyl-2,3-dihydrobenzo[b]-1,4-dioxin-6-carbaldehyde, which upon reaction with dihydropyran in dichloromethane using (PPTS) gave 2-phenyl-3-(tetrahydro-2-pyranyloxy-methyl)-2,3-dihydrobenzo[b]-1,4-dioxin-6-carbaldehyde. This compound by a Wittig reaction with ethoxycarbonylmethylenetriphenylphosphorane gave stereoselectively ethyl 3-[trans-2-phenyl-3-(tetrahydro-2-pyranyloxymethyl)-2,3-dihydrobenzo[b]-1,4-dioxin-6-yl]-2-propenoate, which upon reduction with DIBAL-H afforded the title compound.