Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

نویسندگان

  • Oleksandr Zhurakovskyi
  • Yunus E Türkmen
  • Lorenz E Löffler
  • Vijayalakshmi A Moorthie
  • C Chun Chen
  • Michael A Shaw
  • Mark R Crimmin
  • Marco Ferrara
  • Mushtaq Ahmad
  • Mehrnoosh Ostovar
  • Johnathan V Matlock
  • Varinder K Aggarwal
چکیده

A convergent, nine-step (LLS), enantioselective synthesis of α-cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)-cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N-O cleavage of a bromoisoxazole.

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عنوان ژورنال:

دوره 57  شماره 

صفحات  -

تاریخ انتشار 2018