Formation of Multiple Naturally Occurring Meroterpenoid Scaffolds by the Norrish-Yang Reaction of a p-Benzoquinone

Abstract

The Norrish-Yang reaction, as a typical example, demonstrates the inherent ability of photochemical reaction to facilitate formation of sterically congested C-C bonds, efficiently crafting intricate ring structure in complex organic molecules. Herein we report for the first time a unified synthesis using quinone-based acid-promoted Norrish-Yang photocyclization for the stereoselective construction of multiple avarane-type meroterpenoid natural products.

Keywords: Norrish-Yang reaction; meroterpenoid; p-benzoquinone; photochemistry; total synthesis.