Total Synthesis of (−)-Lycoposerramine-S

Authors

  • Naoaki Shimada,

    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • Dr. Yuzo Abe,

    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • Dr. Satoshi Yokoshima,

    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. Current address: Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601 (Japan)
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  • Prof. Tohru Fukuyama

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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Errata

This article is corrected by:

  1. Errata: Corrigendum: Total Synthesis of (−)-Lycoposerramine-S Volume 53, Issue 34, 8808, Article first published online: 13 August 2014

  • We thank Prof. Hiromitsu Takayama at Chiba University for helpful discussions. This work was financially supported by Grants-in-Aid for Scientific Research (20002004, 22590002) from the Japan Society for the Promotion of Science (JSPS), the Research Foundation for Pharmaceutical Sciences, the Mochida Memorial Foundation for Medical and Pharmaceutical Research, and the Uehara Memorial Foundation.

Abstract

original image

To the core: The first total synthesis of (−)-lycoposerramine-S has been accomplished in 14 steps. The synthesis features the facile construction of the tetracyclic core through an intramolecular 1,3-dipolar cycloaddition of an azomethine ylide, with unexpected stereoselectivity, an 5-exo-trig radical cyclization, and an alkylation of p-nosyl (Ns) amide. TBS=tert-butyldimethylsilyl.

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