Stereocontrolled Total Synthesis of (−)‐Stemaphylline

نویسندگان

  • Ana Varela
  • Lennart K B Garve
  • Daniele Leonori
  • Varinder K Aggarwal
چکیده

Homologation of readily available α-boryl pyrrolidines with metal carbenoids is especially challenging even when good leaving groups (Cl- ) are employed. By performing a solvent switch from Et2 O to CHCl3 , efficient 1,2-metalate rearrangement of the intermediate boronate occurs with both halide and ester leaving groups. The methodology was used in the total synthesis of the Stemona alkaloid (-)-stemaphylline in just 11 steps (longest linear sequence), with high stereocontrol (>20:1 d.r.) and 11 % overall yield. The synthesis also features a late-stage lithiation-borylation reaction with a tertiary amine containing carbenoid.

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عنوان ژورنال:

دوره 56  شماره 

صفحات  -

تاریخ انتشار 2017