Carbocyclic sugars

The cyclitols are a group of carbocyclic sugar derivatives having the general formulation 1,2,3,4,5,6-cyclohexanehexol. How many stereoisomeric cyclitols are possible Draw them in their chair forms. 

M. Aloui, B. Lygo, and H. Trabsa, Observations on the modified Fujimoto-Belleau approach to mannose-derived carbocyclic sugars, Synlett p. 115 (1994). 

This would be a good method for the preparation of carbocyclic sugar analogs, since some sugar analogs have potent biological activities. 

Carbocyclic analogues of furanoid sugars have represented a relevant topic in the realm of carbasugars ever since the discovery of their occurrence as substructures in natural bioactive compounds, such as carbocyclic nucleosides and certain carbocyclic sugar conjugates [2], at... 

Gaudino, J J, Wilcox, C S, A general approach to carbocyclic sugar analogs — preparation of a carbocyclic analog of beta-D-fmctofuranose, Carbohydr. Res., 206(2), 233-250, 1990. 

A synthesis of methylreductic acid (47) and a partial synthesis of uscharin (43) from uscharidin (44) have been performed. No S5mtheses are recorded for the other carbocyclic sugar derivatives. 

Isol. from the cell wall lipopolysaccharide fraction of Pseudomonas caryophylli. Syrup. [a]o +81 (c, 1.75 in H2O). The first known naturally occurring carbocyclic sugar. 

In their studies on mannose-derived carbocyclic sugars, Trabsa and co-workers applied a Wadsworth-Emmons modification of the Fujimoto-Belleau reaction to give a vinyl phosphonate rather than the expected enone. Originally this procedure was used as an alternative to the Ferrier cyclisation, which requires acidic conditions. However, the authors found that the formation of an enone or vinyl phosphonate depended on the carbohydrate stereochemistry. Lactone 21 gave the vinyl phosphonate 22 when treated... 

Racemic 2-azabicyclo[2.2.1]hept-5-ene-3-one has great potential as a synthetic intermediate. The bicyclic lactam is a synthon for carbocyclic sugar amines, carbonucleo-sides, and carbocyclic dinucleotide analogs [239]. Chiral 2-azabicyclo[2.2.1]hept-5-ene-3-one 133 is key intermediate for the synthesis of (—)-carbovir 134, an antiviral agent effective against HIV. Nakano et al. [240] prepared chiral 133 by enantioselective trans-... 

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