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Total Synthesis of Aspergillide A and B Based on the Transannular Oxy-Michael Reaction

Authors

  • Makoto Kanematsu,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505 (Japan), Fax: (+81) 88-633-9575
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  • Dr. Masahiro Yoshida,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505 (Japan), Fax: (+81) 88-633-9575
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  • Prof. Dr. Kozo Shishido

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505 (Japan), Fax: (+81) 88-633-9575
    • Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505 (Japan), Fax: (+81) 88-633-9575
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  • This work was supported financially by a Grant-in-Aid for the Program for Promotion of Basic and Applied Research for Innovations in the Bio-oriented Technology Research Advancement Institution (BRAIN).

Abstract

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Keys to the kingdom: A highly efficient and diastereoselective transannular oxy-Michael reaction for the construction of the syn- and anti-tetrahydropyran units from a common 14-membered macrolactone is the key step for the total synthesis of aspergillide A and B (see scheme; CM=cross-metathesis, HWE=Horner–Wadsworth–Emmons, TBS=tert-butyldimethylsilyl).

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