Base-Mediated Sequential Annulation Reaction of β-Pyrrol-α,β-Unsaturated Compounds with Vinylsulfonium Salts: A New Approach to Polycyclic Pyrrolizine Derivatives

Abstract

In this paper, we reported a novel sequential reaction sequence consisting of two processes including domino [3+2]/[2+1] annulation and in situ Cloke-Wilson rearrangement reaction, which enabled synthesis of a series of structurally complex polycyclic pyrrolizine derivatives in 51–96% yields and excellent diastereoselectivities. The viability of the existing protocol was additionally illustrated by gram-scale synthesis and further modifications. In addition, some of these valuable ring-fused pyrrolizines displayed some extent of anticancer activity, demonstrating their potential application in the medicinal chemistry.