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First Stereoselective Total Synthesis of FD-594 Aglycon

Authors

  • Ritsuki Masuo,

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
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  • Ken Ohmori Dr.,

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
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  • Lukas Hintermann Dr.,

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
    2. Present address: Institut für Organische Chemie, RWTH Aachen (Germany)
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  • Saki Yoshida,

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
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  • Keisuke Suzuki Prof. Dr.

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
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  • This work was partially supported by Global COE program (Chemistry) and a Grant-in-Aid for Scientific Research (JSPS). We are grateful to Daiso Co. Ltd., Osaka, for the generous supply of (R)-(−)-epichlorohydrin.

Abstract

Stereocontrolled access to the hexacyclic core of FD-594 has been achieved. The key steps include the intramolecular SNAr reaction for construction of the densely functionalized xanthone skeleton, the stereoselective lactone cleavage using a chiral nucleophile to induce the axial stereochemistry, and the SmI2-mediated pinacol cyclization for the stereocontrolled conversion of axially chiral biaryl dialdehyde into the corresponding trans diol.

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