Application of 2,3-trans-CHD in Natural-product Syntheses

Because of their suitable skeletal structure trans-CHD are applicable in the synthesis of compound classes of chemical, biological, and pharmaceutical interest. Regio- and stereoselective epoxidation of either one or two double bonds of 2, for example, opens up an approach to a group of naturally occurring cyclohexane ep-oxides which have attracted considerable attention because of their unusual structures, biogenesis, and biological activity [15].

Subsequent nucleophilic opening of the resulting epoxides, or regio- and stereoselective dihydroxylation, affords entry to the class of carbasugars (Scheme 6.4.4); these are of great pharmaceutical interest because of their structural analogy to common sugars, but different biological decomposition. This is also true of amino carbasugars such as valienamine [7b], which, attached to 6-deoxyglucosamine, is the primary active moiety (acarviosine) of the a-glucosidase inhibitor acarbose, and which is also the structural component of other secondary metabolites, for example the adiposins, amylostatins, salbostatin, trestatins, and validamycins. The significance of 2,3-trans-CHD 2 as versatile building block in diversity-oriented synthesis has, therefore, been examined by these types of reaction.

2,3-frans-CHD cyclohexane (amino-)carba epoxides sugars

Scheme 6.4.4. 2,3-trans-CHD 2 as a precursor of cyclohexane epoxides and (amino-) carbasugars.

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