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Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols
Authors:Bellomo Ana  Camarano Soledad  Rossini Carmen  Gonzalez David
Affiliation:a Laboratorio de Síntesis Orgánica, D.Q.O, Fac. de Química, Univ. de la República, C.C. 1157 Montevideo, Uruguay
b Laboratorio de Ecología Química, D.Q.O.—DepBio, Fac. de Química, Univ. de la República, C.C. 1157 Montevideo, Uruguay
Abstract:The first syntheses of two deoxythiocyanocyclitols (4-deoxy-4-thiocyano-l-chiro-inositol and deoxythiocyanoconduritol F) and two deoxysulfonylcyclitol acetals are reported by a chemoenzymatic enantioselective route. The compounds were prepared by a sequence of enzymatic and ruthenium-catalyzed dihydroxylations, and the results were studied regarding reaction conditions and co-catalyst for different derivatives. The new compounds were included in a minilibrary of deoxygenated cyclitols and evaluated for their capacity to influence the feeding behavior of Epilachna paenulata (Coleoptera: Coccinellidae), a common pest of the Curcubitaceae crops.
Keywords:Thiocyanodeoxycyclitol   Dihydroxylation   Insect feeding behavior
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