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Synthesis of metabolites of dapagliflozin: an SGLT2 inhibitor
Dapagliflozin is one of the gliflozin class drugs, useful for the treatment of type-2 diabetes. Dapagliflozin undergoes extensive metabolism and transforms to metabolites in humans. The contribution of pharmacologically active metabolites in drug discovery and development is significant. A streamlined synthetic approach is devised to access three metabolites of dapagliflozin namely, benzylic hydroxy dapagliflozin, oxo dapagliflozin and desethyl dapagliflozin.Two synthetic protocols have been proposed for the synthesis of benzylic hydroxy dapagliflozin and oxo dapagliflozin. An enantioselective deethylation of dapagliflozin is also reported
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A new synthesis of tafamidis
via zinc-MsOH mediated reductive cyclisation strategyA practical zinc-MsOH mediated intra-molecular reductive cyclisation and its application in thesynthesis of tafamidis is presented starting from the readily available 3-hydroxy-4-nitrobenzoic acid as aprecursor. The key reductive cyclization step involves the use of a combination of the readily available zincand MsOH as the catalyst system. This methodology provides an attractive route to 2-aryl benzoxazoles from
ortho -nitro phenols under mild reaction conditions. This methodology is developed on a multi-gram scale andwithout the need for column chromatography.A new and alternative zinc-MsOH mediated intra-molecular reductive cyclisation and its application in the synthesis of tafamidis is reported starting from the readily available 3-hydroxy-4-nitrobenzoic acid as precursor. This method provides an attractive route to 2-aryl benzoxazoles from
ortho -nitro phenols under mild reaction conditions.
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Journal of Chemical Sciences
Volume 135, 2023
All articles
Continuous Article Publishing mode