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Stereochemical Assignment of the 36-Membered Macrolide Ring Portion of Poecillastrin C

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2024, 26, 25, 5290-5294
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    Stereochemical Assignment of the 36-Membered Macrolide Ring Portion of Poecillastrin C
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    • Raku Irie*
      Raku Irie
      Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan
      Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan
      *[email protected]
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      Orcidhttps://orcid.org/0000-0002-8877-4179
    • Yuki Hitora
      Yuki Hitora
      Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan
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    • Ryuichi Watanabe
      Ryuichi Watanabe
      Fisheries Technology Institute, Japan Fisheries Research and Education Agency, 2-12-4 Fukuura, Kanazawa-ku, Yokohama 236-8648, Japan
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      Orcidhttps://orcid.org/0000-0002-6049-6314
    • Hugh Clark
      Hugh Clark
      Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
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    • Yu Suyama
      Yu Suyama
      Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
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    • Shinji Sekiya
      Shinji Sekiya
      Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
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    • Toshiyuki Suzuki
      Toshiyuki Suzuki
      Fisheries Technology Institute, Japan Fisheries Research and Education Agency, 2-12-4 Fukuura, Kanazawa-ku, Yokohama 236-8648, Japan
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    • Kentaro Takada
      Kentaro Takada
      Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan
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      Orcidhttps://orcid.org/0000-0003-3835-1482
    • Shigeki Matsunaga
      Shigeki Matsunaga
      Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan
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    • Seijiro Hosokawa
      Seijiro Hosokawa
      Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
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      Orcidhttps://orcid.org/0000-0002-8036-532X
    • Masato Oikawa
      Masato Oikawa
      Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan
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      Orcidhttps://orcid.org/0000-0002-3919-811X
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    Organic Letters

    Cite this: Org. Lett. 2024, 26, 25, 5290–5294
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    https://doi.org/10.1021/acs.orglett.4c01632
    Published June 12, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    Absolute configuration at 12 stereocenters in the 36-membered macrocyclic ring portion of poecillastrin C (1) was disclosed by chemical degradation and NMR analyses of 1, chemical synthesis, and molecular modeling techniques.

    Copyright © 2024 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c01632.

    • Experimental procedures and analytical data (PDF)

    • Tables of calculated energies and 3JH,H values, a table of correspondences between NOESY cross-peak intensities and calculated H–H distances of X1 (XLSX). Text files of selected computed molecule Cartesian coordinates in.mol and.xyz formats for convenient visualization (TXT). Modeling procedures (PDF) (ZIP)

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    This article is cited by 1 publications.

    1. Hugh Clark, Yuzuki Takahashi, Tadashi Yoneyama, Yu Suyama, Raku Irie, Masato Oikawa, Seijiro Hosokawa. Synthetic Studies on Poecillastrin C: Synthesis of the C14–C35 Segment of the Macrolide Ring Model. The Journal of Organic Chemistry 2025, 90 (6) , 2362-2371. https://doi.org/10.1021/acs.joc.4c02885
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    Organic Letters

    Cite this: Org. Lett. 2024, 26, 25, 5290–5294
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.4c01632
    Published June 12, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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