Synthesis of (±)-Roseophilin

Keywords

(±)-roseophilin - macrocyclic alkaloids - Corey–Chaykovsky reaction - Tsuji–Trost reaction - Dess–Martin oxidation - Friedel–Crafts acylation

Significance

Fürstner and Weintritt report the first synthesis of (±)-roseophilin. This alkaloid possesses a strained macrocyclic entity due to an ansa-bridged bicycle, making it challenging to access. The natural product has been reported to be cytotoxic in vitro against K562 human erythroid leukemia and KB human epidermoid carcinoma cell lines.

 

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Comment

Macrocyclization of allylic alcohol C using the Tsuji–Trost reaction furnished allylic alcohol D. Formation of the ansa-bridged skeleton was enabled through Tsuji–Trost and Friedel–Crafts reactions to form pyrrole G. Finally, 1,2-addition of the organocerium species of I into ketone H established the core of (±)-roseophilin.

 

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Publication History

Article published online:
25 March 2025