Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

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

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Author

Zhurakovskyi, Oleksandr

Türkmen, Yunus E

Löffler, Lorenz E

Moorthie, Vijayalakshmi A

Chen, C Chun

Shaw, Michael A

Crimmin, Mark R

Ferrara, Marco

Ahmad, Mushtaq

Ostovar, Mehrnoosh

Matlock, Johnathan V

Aggarwal, Varinder K

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.