Fürstner A *,
Weintritt H.
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Total Synthesis of Roseophilin.
J. Am. Chem. Soc. 1998;
120: 2817-2825
DOI:
10.1021/ja973846k
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.
