A STEREODIVERGENT ACCESS TO NATURALLY-OCCURRING AMINOCARBASUGARS FROM(PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - TOTAL SYNTHESIS OF PENTA-N,O-ACETYL-(+ -)-VALIDAMINE AND ITS C-1 AND C-2 STEREOISOMERS/
Jl. Acena et al., A STEREODIVERGENT ACCESS TO NATURALLY-OCCURRING AMINOCARBASUGARS FROM(PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - TOTAL SYNTHESIS OF PENTA-N,O-ACETYL-(+ -)-VALIDAMINE AND ITS C-1 AND C-2 STEREOISOMERS/, Journal of organic chemistry, 59(21), 1994, pp. 6419-6424
The total syntheses of the antibiotic component validamine 1 and its t
hree diastereomers 2-4 have been accomplished as their racemic penta-N
,O-acetates via stereocontrolled nucleophilic epoxidation of polyhydro
xylated cyclohexenyl sulfones, obtained from (phenylsulfonyl)-7-oxabic
yclo[2.2.1]heptanes. The diastereoselectivity of the epoxidation can b
e readily controlled by careful choice of the hydroxyl protecting grou
ps. Ring opening of the resulting alpha,beta-epoxy sulfones followed b
y stereocontrolled introduction of an amine precursor led to the four
C-1 and C-2 diastereomers of 1-aminocarbasugars.