Total Synthesis of (+)-Rubriflordilactone A.

Goh SS, Chaubet G, Gockel B, Cordonnier M-CA, Baars H, Phillips AW, Anderson EA

Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium- or cobalt-catalyzed cyclizations to form the CDE rings, and converge on a late-stage synthetic intermediate. These key processes are set up through the convergent coupling of a common diyne component with appropriate AB-ring aldehydes, a strategy that sets the stage for the synthetic exploration of other members of this family of natural products.

Keywords:

Kadsura

,

Schisandra

,

Cobalt

,

Palladium

,

Triterpenes

,

Biological Products

,

Cyclization

,

Catalysis

,

Stereoisomerism