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New Syntheses of E7389 C14−C35 and Halichondrin C14−C38 Building Blocks: Double-Inversion Approach
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    New Syntheses of E7389 C14−C35 and Halichondrin C14−C38 Building Blocks: Double-Inversion Approach
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    Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138
    kishi@chemistry.harvard.edu
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2009, 131, 43, 15636–15641
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    https://doi.org/10.1021/ja9058475
    Published October 6, 2009
    Copyright © 2009 American Chemical Society
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    Abstract

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    With sequential use of catalytic asymmetric Cr-mediated coupling reactions, E7389 C14−C35 and halichondrin C14−C38 building blocks have been stereoselectively synthesized. The C19−C20 bond is first formed via the catalytic asymmetric Ni/Cr-mediated coupling, i.e., 8 + 9 → 10 (90%; dr = 22:1), in which vinyl iodide 8 is used as the limiting substrate. The C23−C24 bond is then formed via the catalytic asymmetric Co/Cr-mediated coupling, i.e., 13 + 14 → 4 (82%; dr = 22:1), in which the alkyl−iodide bond in 14 is selectively activated over the vinyl−iodide bond. The catalytic asymmetric Ni/Cr-mediated reaction is employed to couple C14−C26 segment 19 with E7389 C27−C35 segment 20 (91%; dr = >55:1). In this synthesis, the C23−O bond is stereoselectively constructed via a double-inversion process, i.e., 21 → 22, to furnish E7389 C14−C35 building block 22 in 84% yield. The same synthetic sequence has been employed to synthesize halichondrin C14−C38 building block 18b, i.e., 16a + 19 → 18b.

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    Supporting Information

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    Experimental details, including the syntheses outlined in Schemes 3, 4, 5, 8, 9, and 10, complete characterization of synthetic intermediates, and 1H and 13C NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2009, 131, 43, 15636–15641
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja9058475
    Published October 6, 2009
    Copyright © 2009 American Chemical Society
    Request reuse permissions

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