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Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides.


ABSTRACT: A convergent, nine-step (LLS), enantioselective synthesis of ?-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.

SUBMITTER: Zhurakovskyi O 

PROVIDER: S-EPMC5817397 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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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. ...[more]

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