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Asymmetric Total Synthesis of (−)-Maldoxin, a Common Biosynthetic Ancestor of the Chloropupukeananin Family

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    Asymmetric Total Synthesis of (−)-Maldoxin, a Common Biosynthetic Ancestor of the Chloropupukeananin Family
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    Organic Letters

    Cite this: Org. Lett. 2018, 20, 13, 3919–3922
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    https://doi.org/10.1021/acs.orglett.8b01502
    Published June 8, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    The total synthesis of pestheic acid based on an intramolecular SNAr reaction without a nitro group and the asymmetric synthesis of (−)-maldoxin by a catalytic enantioselective oxidative dearomatization of pestheic acid are described. The reactivity of (−)-maldoxin as a diene in the Diels–Alder reaction is also investigated.

    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.orglett.8b01502.

    • Detailed experimental procedures, spectroscopic data, 1H and 13C NMR spectra, and X-ray crystallographic data of new compounds (PDF)

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    CCDC 1829379 and 1833157 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

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    This article is cited by 24 publications.

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    12. Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents. Chinese Journal of Organic Chemistry 2023, 43 (11) , 3784. https://doi.org/10.6023/cjoc202304008
    13. Takahiro Suzuki. Total Syntheses of Chloropupukeananin and Its Related Natural Products. Organics 2022, 3 (3) , 304-319. https://doi.org/10.3390/org3030023
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    18. Ravi Kumar, Fateh V. Singh, Naoko Takenaga, Toshifumi Dohi. Asymmetric Direct/Stepwise Dearomatization Reactions Involving Hypervalent Iodine Reagents. Chemistry – An Asian Journal 2022, 17 (4) https://doi.org/10.1002/asia.202101115
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    24. Toshifumi Dohi, Kotaro Kikushima, Hideyasu China. Asymmetric Construction of Heterocycles via Dearomative Coupling and Addition Reactions of Phenol and Aniline Derivatives. HETEROCYCLES 2019, 98 (11) , 1489. https://doi.org/10.3987/REV-19-916
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    Organic Letters

    Cite this: Org. Lett. 2018, 20, 13, 3919–3922
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.8b01502
    Published June 8, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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