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.
Highlights
Indole alkaloids have long been a source of inspiration for the development of new synthetic methods and strategies. aCyclopiazonic acid (a-CPA, 1) is a prenylated indole alkaloid produced by a number of Penicillium species including P. commune, P. griseofulvum, and P. camemberti.[1]
It is a potent inhibitor of Ca2+-dependent ATPase (SERCA) which prevents calcium reuptake in muscle.[2]
In addition to its significant biological activity, a-CPA-producing fungi are found in cheese, meat, and other dietary products, making it important to the food industry
Summary
Indole alkaloids have long been a source of inspiration for the development of new synthetic methods and strategies. aCyclopiazonic acid (a-CPA, 1) is a prenylated indole alkaloid produced by a number of Penicillium species including P. commune, P. griseofulvum, and P. camemberti.[1]. Sulfonium salts 15 a,b were prepared from known alcohol 21[14] by a two-step sequence via triflate 22 (Scheme 1 B).
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