Four tetrahydrofuran rings in one step can be constructed with the multiple five-mem-bered-ring-selective Williamson reaction (1 → 2). The tetratosylate 1 is obtained from the corresponding dialkyne by a reagent-controlled, diastereoselective dihy-droxylation. This reaction sequence opens up an efficient route to enantiomerically pure oligo(tetrahydrofuran)s.
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Wagner et al. (1994) studied this question.
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