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Synlett 1996; 1996(2): 131-134
DOI: 10.1055/s-1996-5342
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Stereocontrolled Synthesis of Highly Functionalized 2,4-Dioxahydrindans via Debenzylating Tetrahydrofuran Ring Formation1

Abu T. Khan, Hansjörg Dietrich, Richard R. Schmidt*
  • *Fakultät für Chemie, Universität Konstanz, Postfach 5560 M 725, D-78434 Konstanz, Germany
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Publikationsdatum:
31. Dezember 2000 (online)

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4C-(1-Hydroxyalkyl)-substituted 2,3,6-tri-O-benzylglucopyranosides (S)-2a, (R)-2a, and 6 are transformed at low temperature into the corresponding triflates; they undergo immediately an SN2-type reaction leading to the formation of a trans-fused tetrahydrofuran ring under loss of the 6-O-benzyl group, thus yielding 2,4-dioxahydrindans (R)-3a, (S)-3a, and 7, respectively. 4C(α-Hydroxyallyl) and 4C(α-hydroxybenzyl) derivatives of 2 lead to 6-O-debenzylation and triflate/hydride exchange reactions, thus yielding entirely different reaction products.

Ring closure, dealkylation - branched sugars - deprotection, regioselective - dioxahydrindans, trans-fused