Convergent Total Syntheses of (-)-Rubriflordilactone B and (-)-pseudo-Rubriflordilactone B

Abstract

A highly convergent strategy for the synthesis of the natural product (-)-rubriflordilactone B, and the proposed structure of (-)-pseudo-rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium-catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the identity of pseudo-rubriflordilactone B and provides a robust platform for further synthetic and biological investigations.

Keywords: cyclotrimerization; natural products; schinortriterpenoids; structure elucidation; total synthesis.