An efficient constructive method for a tricyclic system: an important intermediate for the synthesis of tricycloclavulone

Synthesis of Chiral Cyclopentenones

“…The first enantioselective total synthesis of (+)-tricycloclavulone was reported by Iguchi and co-workers (Scheme ). In previous work, the same research group prepared the tricyclic core in a racemic form …”

“…610 In previous work, the same research group prepared the tricyclic core in a racemic form. 611 This synthesis began by applying an enantioselective [2+2]cycloaddition, catalyzed by the chiral bis-py CuCl 2 catalyst 1367 in the presence of AgSbF 6 , affording 1372 in 73% ee. The tricyclic core 1373 was formed on RCM condensation with the second-generation Grubbs catalyst 612 in 56% yield.…”

The [4 + 3]-Cycloaddition/Quasi-Favorskii Process. Synthesis of the Carbocyclic Core of Tricycloclavulone

“…Recently, Iguchi and co-workers reported the isolation of tricycloclavulone ( 1 ) from the Okinawan soft coral Clavularia viridis . Soon afterward, they reported the enantioselective total synthesis of this compound . While no biological activity has been reported for 1 , it is a structurally intriguing compound, related to and possibly derived from clavulone III ( 2 ), one of a number of marine prostanoids with diverse and important bioactivity …”

Enantioselective Total Synthesis of (+)-Tricycloclavulone

“… The first total synthesis of (+)-tricycloclavulone having a unique tricyclo[5,3,0,0 , ]decane skeleton and six chiral centers was achieved in a highly stereoselective manner. It includes a catalytic enantioselective [2+2]-cycloaddition reaction using novel chiral copper catalyst, extremely effecting an intramolecular ester transfer reaction, and asymmetric reduction of the carbonyl group on the α-chain using Noyori's chiral ruthenium catalyst.…”