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Stereoselective total synthesis of (−)-brevisamide
Authors:JS Yadav  N Mallikarjuna ReddyMd Ataur Rahman  AR PrasadBV Subba Reddy
Institution:Centre for Semiochemicals, CSIR, Indian Institute of Chemical Technology, Hyderabad 500007, India
Abstract:The stereoselective total synthesis of (−)-brevisamide, a novel marine cyclic ether alkaloid isolated from dinoflagellate karenia brevis is described. The key steps involved in this synthesis are the Sharpless asymmetric epoxidation and regioselective ring opening of chiral epoxide by Gilman's reagent. The tetrahydropyran core has been constructed by an intramolecular SN2 cyclisation.
Keywords:Sharpless asymmetric epoxidation  Gilman's reaction  SN2 cyclisation  TEMPO-BIAB oxidation  Horner&ndash  Wadsworth&ndash  Emmons reaction
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