COMMUNICATIONSdroxylated with OsO,/N-methylmorpholine-N-oxide which resulted in two diols 10 and 13 in a ratio of 1 : 1 . The chiral centers of olefin 9. therefore, have no controlling influence on the dihydroxylation. The observed stereocontrol is due solely to the Sharpless dihydroxylation reagent. Diols 10 and 13 can be converted by a multiple five-membered-ring-selective Williamson reaction analogous to the reaction in Scheme 2 into the dimeric tetrahydrofuranols 11 and 14, respectively, and subsequently to the corresponding disilyl ethers 12 and 15.The enantiomerically pure alkenes 4 and 9 were prepared by standard methods (Scheme 4). The double alkylation of acetylene with bromide 1619] and the subsequent (E)-selective reduction to the olefin yielded compound 9. Reaction of two equivalents of alkyne 19 with one equivalent of dibromide 18"01 and subsequent (E)-selective reduction to the olefin yielded diene 4.The synthetic sequence of reagent-controlled, diastereoselective dihydroxylation and multiple five-membered-ring-selective Williamson reaction presented here opens up an efficient, bidirectional route to the enantiomerically pure oligo(tetrahydr0-furan)s.