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Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin

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    Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin
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    Organic Letters

    Cite this: Org. Lett. 2018, 20, 11, 3286–3290
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    https://doi.org/10.1021/acs.orglett.8b01156
    Published May 17, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    A diastereoselective palladium-catalyzed cyclization of allenyl hemiacetals is described. It permits the selective synthesis of 1,3-dioxane derivatives, precursors for syn-configured 1,3-diols which make an appearance in all of the statin representatives. The reaction allows the total synthesis of Rosuvastatin and Pitavastatin in a straightforward fashion.

    Copyright © 2018 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.8b01156.

    • Experimental procedures and analytical data for the synthesized compounds, including 1H and 13C NMR spectra (PDF)

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    CCDC 1573385 contains 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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    This article is cited by 21 publications.

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    Organic Letters

    Cite this: Org. Lett. 2018, 20, 11, 3286–3290
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.8b01156
    Published May 17, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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