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.
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Zhurakovskyi, O., Türkmen, Y. E., Löffler, L. E., Moorthie, V. A., Chen, C. C., Shaw, M. A., … Aggarwal, V. K. (2018). Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides. Angewandte Chemie - International Edition, 57(5), 1346–1350. https://doi.org/10.1002/anie.201712065
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