Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides.
Oleksandr ZhurakovskyiYunus Emre TürkmenLorenz E LöfflerVijayalakshmi A MoorthieC Chun ChenMichael A ShawMark R CrimminMarco FerraraMushtaq AhmadMehrnoosh OstovarJohnathan V MatlockVarinder Kumar AggarwalPublished in: Angewandte Chemie (International ed. in English) (2018)
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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