Enantioselective Synthesis Of 2,6-dideoxy Carbasugars Basedon A Desymmetrizing Hydroformylation-carbonyl Ene Cyclization Process

摘要

A practical one-pot process involving a desymmetrizing hydro-formylation with the aid of a chiral catalyst-directing group (CDG~*), followed by a carbonyl ene cyclization provides a straightforward access to both enantiomers of the resulting cyclohexanediol; further divergent, highly selective and protecting group-free transformations furnish the carbocyclic analogues of four important 2,6-dideoxysugars.rnThe bioactivity of many naturally occurring antibiotics and antitumor agents is strongly depending on their glycosidic components. Over the past years it has been demonstrated that the structure of the sugar moieties affects the compound's specificity, substrate binding and pharmacology.