A Short and Efficient Synthesis of Neodysiherbaine A by Using Catalytic Oxidative Cyclization

Authors

  • Prof. Timothy J. Donohoe,

    Corresponding author
    1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-708
    • Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-708
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  • Paul C. M. Winship,

    1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-708
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  • Matthew R. Tatton,

    1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-275-708
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  • Dr. Peter Szeto

    1. GlaxoSmithKline Research & Development Limited, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY (UK)
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  • We would like to thank the EPSRC/Pharma Organic Synthetic Chemistry Studentships program for supporting this project and GlaxoSmithKline for financial support. We also thank Diamond Light Source for an award of beamtime on I19 (MT1858) and Dr. K. E. Christensen for support.

Abstract

original image

To the point: The synthesis of the title compound was achieved with 24 % overall yield through a sequence that has just seven linear steps (see scheme). Key points are the facial selectivity displayed by an oxocarbenium ion derived from a ribopyranose system and an osmium-catalyzed oxidative cyclization that is compatible with several acid-sensitive groups.

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