Total syntheses of (±)-penicibilaenes A and B via intramolecular aldol condensation

In this study, concise total syntheses of Peniclillium sesquiterpenes (+/-)-Penicibilaenes A and B are described. This approach involves an effective intramolecular aldol condensation to construct a bicyclic skeleton, a stereoselective rhodium-catalyzed 1,4-addition, a ring-closing metathesis, and several effective transformations that lead to (+/-)-penicibilaenes A and B with longest linear sequences of 12 and 13 steps, respectively. These transformations utilize commercial materials and are achieved in 4.0% overall yields for both compounds.

Automated summary

This study describes the concise total syntheses of Peniclillium sesquiterpenes (+/-)-Penicibilaenes A and B, achieved through efficient intramolecular aldol condensation, stereoselective rhodium-catalyzed 1,4-addition, ring-closing metathesis, and effective transformations. The longest linear sequences for the synthesis of (+/-)-penicibilaenes A and B are 12 and 13 steps, with an overall yield of 4.0% for both compounds.