Asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol [(+)-ADGDP] |
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Authors: | Stephen G Davies Aude LA FigucciaAi M Fletcher Paul M RobertsJames E Thomson |
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Institution: | Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK |
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Abstract: | The asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol (+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol (+)-ADGDP] were achieved via the ring-closing iodoamination of an enantiopure bishomoallylic amine, followed by functionalisation of the resultant iodomethyl substituted pyrrolidine. In the case of (+)-DGDP, formation of the corresponding aziridinium ion followed by regioselective ring-opening with H2O gave the desired hydroxymethyl substituted pyrrolidine as a single diastereoisomer (>99:1 dr), with subsequent deprotection giving (+)-DGDP in good yield. Whereas in the case of (+)-ADGDP, displacement of iodide with NaN3 proved to be optimal, giving (+)-ADGDP in good yield after reduction and deprotection. |
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Keywords: | (+)-DGDP (+)-ADGDP Pyrrolidine alkaloids Asymmetric synthesis |
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