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

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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 date19 Dec 2017
DOIs
Publication statusPublished - 26 Jan 2018

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