Total Syntheses of (-)-Minovincine and (-)-Aspidofractinine through a Sequence of Cascade Reactions

Abstract

We report 8-step syntheses of (-)-minovincine and (-)-aspidofractinine using easily available and inexpensive reagents and catalyst. A key element of the strategy was the utilization of a sequence of cascade reactions to rapidly construct the penta- and hexacyclic frameworks. These cascade transformations included organocatalytic Michael-aldol condensation, a multistep anionic Michael-S_N 2 cascade reaction, and Mannich reaction interrupted Fischer indolization. To streamline the synthetic routes, we also investigated the deliberate use of steric effect to secure various chemo- and regioselective transformations.

Keywords: alkaloids; asymmetric catalysis; biomimetic synthesis; organocatalysis; total synthesis.