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Natural Products Chemistry III pp 89–106Cite as

Novel Carbohydrate Transformations Discovered en Route to Natural Products

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Abstract

Progress in the synthesis of the ansa chain of streptovaricin A is discussed. The target molecule is an 11-carbon array containing 9 contiguous chiral centers, 2 of which are tertiary alcohols, and a third is a methoxycarbonyl group. The synthesis begins with levoglucosan (1,6-anhydro-β-D-glucopyranose), which by a process of pyranosidic homologation, is elaborated into a dipyranoside, and thence a tripyranoside which carries eight of the nine chiral centers. The ninth is installed by an acyclic stereoselective process.

There are two digressions. The first describes a convergent strategy to multiple contiguous chiral centers which involves aldol condensation of two sugars. The second reports a procedure for chemoselective activation of the anomeric oxygen.

Complex natural products present excellent opportunities for organic chemists to exercise their creative skills, and also for testing the limits of current synthetic methodology. In the course of these adventures, unexpected reactions are almost certain to occur, and although these are initially unwanted, it is from such reactions that new science arises. The very fact that they were “unexpected” means that the potential exists for the advancement of the discipline, even more so than might have been accomplished by the initial undertaking. In this lecture, I hope to discuss such a situation--our progress toward a complex natural product, and the benefits of some “unexpected” reactions.

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Author information

Authors and Affiliations

  1. Department of Chemistry, Paul M. Gross Chemical Laboratory, Duke University, Durham, North Carolina, 27706, USA

    B. Fraser-Reid, R. Mootoo, V. Date & S. Handa

Authors
  1. B. Fraser-Reid
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  2. R. Mootoo
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  3. V. Date
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  4. S. Handa
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Editor information

Editors and Affiliations

  1. HEJ Research Institute of Chemistry, University of Karachi, Karachi-32, Pakistan

    Atta-ur-Rahman

  2. Department of Chemistry, Northeastern University, 360 Huntington Avenue, Boston, MA, 02115, USA

    Philip William Le Quesne

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© 1988 Springer-Verlag Berlin Heidelberg

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Fraser-Reid, B., Mootoo, R., Date, V., Handa, S. (1988). Novel Carbohydrate Transformations Discovered en Route to Natural Products. In: Atta-ur-Rahman, Le Quesne, P.W. (eds) Natural Products Chemistry III. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-74017-6_5

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  • DOI: https://doi.org/10.1007/978-3-642-74017-6_5

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-74019-0

  • Online ISBN: 978-3-642-74017-6

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