Synthesis of the Tetracyclic Framework of Polycyclic Spiro Lignan Natural Products

Abstract

Polycyclic spiro lignans are a new family of lignan natural products recently isolated from Gymnotheca involucrata. The first synthesis of two model substrates of this rare family of natural products was achieved in six steps. An efficient strategy that features Suzuki coupling and Friedel-Crafts acylation was employed to construct the ABC tricyclic fluorene framework. Subsequently, Grignard reaction followed by acid-mediated cyclization furnished the spiro cyclic ether ring D.