Synthesis of a protected enantiomerically pure 2-deoxystreptamine derivative from D-allylglycine

Abstract

A diastereoselective synthetic route from D-allylglycine to the enantiopure (protected) 2-deoxystreptamine derivative 14 is presented. Key steps involve two consecutive chain extensions-with crucial stereodirective roles for the amino protective groups, ring closure by olefin metathesis, face selective dihydroxylation, cyclic sulfate formation and finally opening with azide. The resulting 2-deoxystreptamine derivative is ideally protected for the preparation of 4,5- or 4,6-linked aminoglycoside antibiotics. (C) 2004 Elsevier Ltd. All rights reserved.