Rapid Total Syntheses Utilizing “Supersilyl” Chemistry

Authors

  • Dr. Brian J. Albert,

    1. Department of Chemistry, The University of Chicago, 5735 S Ellis Avenue, Chicago, IL 60637 (USA), Fax: (+1) 773-702-0805
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  • Dr. Yousuke Yamaoka,

    1. Department of Chemistry, The University of Chicago, 5735 S Ellis Avenue, Chicago, IL 60637 (USA), Fax: (+1) 773-702-0805
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  • Prof. Dr. Hisashi Yamamoto

    Corresponding author
    1. Department of Chemistry, The University of Chicago, 5735 S Ellis Avenue, Chicago, IL 60637 (USA), Fax: (+1) 773-702-0805
    • Department of Chemistry, The University of Chicago, 5735 S Ellis Avenue, Chicago, IL 60637 (USA), Fax: (+1) 773-702-0805
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  • This work was made possible by the generous support of the NIH (P50 GM086 145-01) and a Uehara Foundation fellowship (Y.Y.). We would additionally like to thank Antoni Jurkiewicz for his NMR expertise and Chang-Jin Qin for his assistance with mass spectrometry.

Abstract

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In short order: The shortest total syntheses of natural product EBC-23 (see scheme, PMB=para-methoxybenzyl, TMS=trimethylsilyl) and a polymethoxy-1-alkene to date have been accomplished in just ten total steps each from commercially available chemicals. The syntheses took advantage of highly diastereoselective supersilyl-directed cascade polyaldol reactions.

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