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Synfacts 2022; 18(05): 0459
DOI: 10.1055/s-0041-1738021
Synthesis of Natural Products and Potential Drugs

Synthesis of Four Kopsane Alkaloids

Contributor(s):
Erick M. Carreira
,
Moritz E. Hansen
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
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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.


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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.


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Publication History

Article published online:
20 April 2022

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