Total Synthesis of (±)-Lycojapomines A and B

Keywords

(±)-lycojapomine A and B - lycopodium alkaloids - photoinduced radical cyclization - 5-endo-dig cyclization - aza-silyl-Prins reaction - ozonolysis

Significance

Gross and Stoltz report the total synthesis of the two lycopodium alkaloids, (±)-lycojaponin A and (±)-lycojaponin B. The strategy hinges on a photoinduced dearomative radical cyclization and subsequent Ag(I) cyclization cascade to forge the tricyclic core of the molecules. The route diverges late-stage via an aldol reaction under either kinetic or thermodynamic control.

 

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Comment

The synthesis commenced with functionalization of pyrrole A, affording urea B. Photoinduced radical cyclization of B furnished enamine C. Following fragment coupling to access ynone E, treatment of the latter with Ag(I) triggered the key cyclization cascade. After functional group manipulation of enone G to hemiacetal I, the two natural products were obtained via aldol reactions.

 

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Publikationsverlauf

Artikel online veröffentlicht:
27. August 2025