Total Synthesis of Both Methyl 4a-Carba-<scp>d</scp>-arabinofuranosides

Abstract

[reaction: see text] The total synthesis of methyl 4a-carba-alpha-D-arabinofuranoside (1) and methyl 4a-carba-beta-D-arabinofuranoside (2) has been achieved starting from D-mannose (5). Key transformations included a ring-closing metathesis of diene 11 employing Schrock's catalyst followed by a stereoselective hydrogenation with Wilkinson's catalyst.