L. Bertelli et al., DIVERGENT ASYMMETRIC-SYNTHESIS OF ERYTHRO-3-AZIDO-1,2-EPOXIDES OR THREO-3-AZIDO-1,2-EPOXIDES FROM THE SAME 2,3-EPOXY-1-ALKANOL - A CONVENIENT SYNTHESIS OF STATINE AND ITS 3-EPIMER, Gazzetta chimica italiana, 123(9), 1993, pp. 521-524
A 2,3-epoxy-1-alkanol (obtained by Sharpless asymmetric epoxidation of
the corresponding allylic alcohol), O-protected with a 2-methoxypropy
l group, undergoes highly regioselective oxirane ring opening by attac
k of azide ion at C-3 to afford a monoprotected azidodiol which can be
elaborated to divergently give either threo-or erythro-3-azido- 1,2-e
poxide. An application to the synthesis of the natural amino acid stat
ine, 24, and of its 3-epimer, 26, is described.