Carbocyclic Ring Closure of an Aminodeoxy HEX-5-Enopyranoside
- 1 September 1985
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 4 (3) , 323-331
- https://doi.org/10.1080/07328308508070183
Abstract
Ferrier''s intramolecular carbocyclic ring closure reaction of methyl 3,4-di-O-acetyl-2-benzoylamino-2,6-dideoxy-.alpha.-D-xylo-hex-5-enopyranoside (2) led to 2L-2,4,5/3-2,3-di-O-acetyl-4-benzoylamino-5-hydroxycyclohexanone (4). Upon acetylation compound 4 underwent .beta.-elimination to give the conjugated enone 5. The convenient preparation of these highly functionalized aminocyclohexanones offers an efficient route to monoamino- or 1,4-diaminocyclitol-type aminoglycoside antibiotic aglycones, starting from 2-amino-2-deoxy-D-glucose.This publication has 12 references indexed in Scilit:
- Synthesis of two enantiomeric tetrasubstituted cyclohexanones from 6-deoxyhex-5-enopyranoside derivativesCarbohydrate Research, 1985
- Hydroxy group directed hydrogenation with rhodium and iridium catalysts. Synthesis of a protected chiral carbocyclic analogue of daunosamineJournal of the Chemical Society, Chemical Communications, 1985
- A novel approach to aminocyclitol analogues from azidotrideoxyhex-5-enopyranosidesJournal of the Chemical Society, Chemical Communications, 1984
- A simple synthesis of epimeric 2-azidoinosose derivativesCarbohydrate Research, 1983
- A General Synthesis of Cyclitols and Aminocyclitols from CarbohydratesSynthesis, 1983
- Synthesis of potential antimicrobial agents from maltose. Part II. Partial conversion of maltose into cyclohexane derivatives.Agricultural and Biological Chemistry, 1981
- Unsaturated carbohydrates. Part 21. A carbocyclic ring closure of a hex-5-enopyranoside derivativeJournal of the Chemical Society, Perkin Transactions 1, 1979
- Nucleophilic replacement reactions of sulphonatesCarbohydrate Research, 1972
- A new synthesis of a 2,3-epimino-α-D-allopyranosideCarbohydrate Research, 1965
- Some Fatty Acid Derivatives of D-GlucosamineJournal of the American Chemical Society, 1956