Formation of Multiple Naturally Occurring Meroterpenoid Scaffolds by the Norrish‐Yang Reaction of a <i>p</i> ‐Benzoquinone
Bing‐Yan Liu, Zi‐Chun Zhang, Zhi‐Lin Song, Hong‐Yi Yuan, Hongyi Yuan, Zhong‐Chao Zhang, Zhen Yang
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.
Topics & Concepts
QuinoneSteric effectsBenzoquinoneStereoselectivityChemistryRing (chemistry)MoleculeStereochemistryPhotochemistryOrganic chemistryCatalysisPhotochromic and Fluorescence ChemistryOxidative Organic Chemistry ReactionsRadical Photochemical Reactions