Synthesis of potassium 2,3,4-trihydroxy-2-methylbutanoate: a leaf-closing substance of Leucaena leucocephalam |
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| Authors: | Sanjib Gogoi |
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| Institution: | Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India |
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| Abstract: | Starting from citraconic anhydride (2), a six step synthesis of leaf closing substance (±)-erythro potassium 2,3,4-trihydroxy-2-methyl-butanoate (1) has been described with 29% overall yield via diesterification, OsO4-dihydroxylation, acetonide protection, regioselective mono hydrolysis of unhindered ester moiety, borane-dimethylsulfide induced chemoselective reduction of carboxylic group and hydrolysis pathway. Surprisingly, the sodium borohydride reduction of monoester 5 and lithium borohydride reduction of 11 furnished the undesired regioisomer 7. |
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| Keywords: | Citraconic anhydride Regioselective hydrolysis Chemoselective reduction Leaf-closing substance Potassium 2 3 4-trihydroxy-2-methylbutanoate Synthesis |
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