Qin B,
Lu Z,
Jia Y.
*
Peking University Beijing, P. R. of China
Divergent Total Synthesis of Four Kopsane Alkaloids:
N-Carbomethoxy-10,22-dioxokopsane, Epikopsanol-10-lactam, 10,22-Dioxokopsane, and
N-Methylkopsanone.
Angew. Chem. Int. Ed. 2022; e202201712
DOI:
10.1002/anie.202201712
Key words
kopsane alkaloids - Vilsmeier–Haack reaction - Diels–Alder cycloaddition - aldol addition
Significance
The kopsanes are a family of heptacyclic alkaloids. Jia and co-workers report a divergent and enantioselective synthesis of four members based on a common intermediate.
Comment
Ruthenium-catalyzed dihydroxylation of vinyl chloride G and reductive enolization with concomitant aldol addition followed by oxidation yields diketone H, which is elaborated to the common heptacyclic intermediate K.
