Syntheses of (–)-Scabrolide A and (–)-Yonarolide

Key words

(–)-scabrolide A - (–)-yonarolide - norcembranoid terpenoids - Ni-catalyzed annulation - Riley oxidation - Liebeskind–Srogl coupling - intramolecular Michael addition/elimination

Significance

Sarlah and co-workers report the total syntheses of (–)-scabrolide A and (–)-yonarolide, two norcembranoid terpenoids. The natural products feature a 5/6/7-fused carbocyclic ring system and an additional γ‑lactone.

Comment

Bicyclic lactone F is accessed by Ni‑catalyzed annulation using cyclopropane C and subsequent fragmentation. The two building blocks F and H were fused in a Liebeskind–Srogl coupling. An intramolecular Michael addition elimination cascade using a zinc-amido base furnishes enone L.

Publication History

Article published online:
16 June 2023