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.

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.

Publication History

Article published online:
25 March 2025