Stereoselective synthesis of new conduramines and aminocyclitol derivatives

Triacetate of 7-oxabicyclo[2.2.1]hept-5-ene-1,2-exo,3-exo-trimethanol was converted selectively into (1RS,2SR,5RS,6RS)-4,5,6-tris(acetoxymethyl)-2-bromocyclohex-3-en-1-ol (4) or into (1RS,2SR,5RS,6RS)-5,6-bis(acetoxymethyl)-2-bromo-4-bromomethylcyclohex-3 -en-1-ol (12). These products were displaced with azide anion and transformed into (1RS,2RS,5RS,6RS)-2-amino-4,5,6-tris(hydroxymethyl)cyclohex-3-en-1-ol (7) and (1RS,2RS,5RS,6RS)-2-amino-4-aminomethyl-5,6-bis(hydroxymethyl)cyclohex-3 -en-1-ol (15), respectively. (1RS,2SR,3RS,4SR,5RS,6SR)-3-Amino-1,5,6-tris(hydroxymethyl)cyclohexa-1,2 ,4-triol (11) was also derived from 4.