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/

Authors
ACENA JL ARJONA O DELAPRADILLA RF PLUMET J VISO A
Citation
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
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
21
Year of publication
1994
Pages
6419 - 6424
Database
ISI
SICI code
0022-3263(1994)59:21<6419:ASATNA>2.0.ZU;2-0
Abstract
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.