Lewis acid mediated diastereoselective synthesis of fused fluorinated & non fluorinated spiroketal: As potential biologically active unnatural products

Oluropo C Agbaje, Tennessee State University

Abstract

The selective introduction of one or more fluorine atoms into specific positions in organic molecule changes the molecules physicochemical properties, including its stability, lipophilicity and bioavailability. The above behavior could be explained by the unique physical and biological properties of fluorine. The carbon-fluorine bond is generally stronger than the carbon-hydrogen bond. Thus many fluorine-containing compounds are stable and often avoid undesirable metabolic transformations. In addition, the increased lipophilicity often leads to ease of absorption and transportation of molecules within biological membranes, thereby improving their overall pharmacokinetic and pharmacodynamic properties. A one-pot Diels-Alder reaction for the synthesis of a fused fluorinated and non fluorinated spiroketal from derivative of cyclichexane-1,3-diones and diarylideneacetone in the presence of one equivalent of ZnCl2, has been developed. Lewis acid mediated initial formations of a Michael adduct underwent intermolecular cyclization. The diastereoselectivity of the reaction using different Lewis acids, solvents, temperature, time, was systematically investigated. The mechanisms and factors controlling the stereoselectivity was studied and discussed.^

Subject Area

Chemistry, Organic|Chemistry, Pharmaceutical

Recommended Citation

Oluropo C Agbaje, "Lewis acid mediated diastereoselective synthesis of fused fluorinated & non fluorinated spiroketal: As potential biologically active unnatural products" (2009). ETD Collection for Tennessee State University. Paper AAI1467918.
http://digitalscholarship.tnstate.edu/dissertations/AAI1467918

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