An efficient method for the synthesis of hydrocyclopenta[1,2-b]furan with various side chains at 3a-position

(3aS∗,1aR∗)-1a-Methoxy-3a-methoxycarbonyl-2,3,4,5,6,3a-hexahydrocyclopenta1,2-b]furan was prepared in 96% overall yield from 2-methoxycarbonylated cyclopenta-1-one in two steps. This furan derivative is used as a divergent intermediate in the synthesis of our originally designed chiral resolving agents having various substitutions. During the preliminary evaluation of divergent synthetic products, it was discovered that 3a-(fluoren-9-ylidenemethyl)-2,3,4,5,3a-pentahydrocyclopenta1,2-b]furan, was a remarkably improved chiral resolving agent for secondary alcohols.