Biological activity of carbocyclic polyhydroxylated derivatives is very well documented. We are interested in the synthesis of optically pure polyhydroxylated decalin derivatives of type 1, which can be regarded as carbocyclic sugar mimics with rigid structure. The chiron approach leading to derivatives of type 1 from simple sugars is presented in scheme 1 (exemplified by transformations of D-glucose) [1].

[Scheme 1]

In the synthetic route we employed a highly stereoselective transformation of sugar allyltin derivative 2 to dienoaldehyde 3. The bicyclic structure of 4 was obtained in the intramolecular Diels-Alder cycloaddition. Further stereoselective functionalization of an allylic fragment via selenium compounds [2] led to polyhydroxylated decalins 5. The mechanism of the processes will be discussed.

[1] Jarosz, S.; Gaweł A. Eur. J.Org. Chem. 2005, 3415.

[2] Jarosz, S.; Nowogródzki, M. J. Carbohydr. Chem. 2006, 25, 139.

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1. Stereoselective synthesis of highly oxygenated derivatives decalins and cyclohexanes from monosaccharides
2. Synthesis of higher carbon sugars. Unexpected rearrangement of higher sugar allylic alcohols