Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the <span style="font-variant: small-caps">d</span>-<i>gluco</i> and <span style="font-variant: small-caps">d</span><i>-xylo-</i> Derived Trienes

Abstract

2,3,4-Tri-O-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cyclization even under high pressure.

Keywords

• bicyclic sugar mimetics
• stereoselective synthesis
• Diels−Alder reaction
• Wittig-type reaction