Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

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*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

28 Citations (Scopus)
235 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)1346–1350
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number5
Early online date9 Jan 2018
DOIs
Publication statusPublished - 22 Jan 2018

Keywords

  • (3+2)-cycloaddition
  • Aziridination
  • Sulfur ylide
  • Total synthesis
  • α-cyclopiazonic acid

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