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Syntheses of (−)-Tripterifordin and (−)-Neotripterifordin from Stevioside

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    Syntheses of (−)-Tripterifordin and (−)-Neotripterifordin from Stevioside
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    Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, 5-16-1 Ohmiya, Asahi-ku, Osaka 535-8585, Japan
    *Tel: +81-6-6954-4081. Fax: +81-6-6954-4081. E-mail: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2018, 83, 3, 1606–1613
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    https://doi.org/10.1021/acs.joc.7b02916
    Published January 12, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    We report short syntheses of (−)-tripterifordin and (−)-neotripterifordin, potent inhibitors of HIV replication, from stevioside, a natural sweetener used worldwide. The key transformations are reduction at C13 through the formation of a tertiary chloride and subsequent three-step lactonization including a selective iodination at C20 by the photoreaction of the C19-alcohol. The title compounds were reliably obtained from stevioside in 9 and 11 steps (with 5–7 isolation steps), respectively. Additionally, the related lactone-containing ent-kaurenes, doianoterpenes A and B, and two more natural products were synthesized.

    Copyright © 2018 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.7b02916.

    • Comparisons of 13C NMR data of natural and synthetic compounds (Tables S1 and S2), and 1H and 13C NMR spectra of all synthetic compounds (PDF)

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2018, 83, 3, 1606–1613
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.7b02916
    Published January 12, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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