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Concise Total Synthesis of the Frog Alkaloid (−)-205 B

Authors

  • Sergey V. Tsukanov,

    1. Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, NC 27695-8204 (USA)
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  • Prof. Dr. Daniel L. Comins

    Corresponding author
    1. Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, NC 27695-8204 (USA)
    • Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, NC 27695-8204 (USA)
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Abstract

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Highly stereocontrolled: The total synthesis of frog alkaloid (−)-205B features a chiral N-acylpyridinium salt reaction and an unprecedented trifluoroacetic anhydride mediated addition of an allylstannane to a vinylogous amide. The core was assembled using a Tsuji–Trost allylic amination reaction and a ring-closing metathesis. TIPS=triisopropylsilyl.

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