Catalytic Asymmetric Synthesis of Chiral Benzofuranones

Abstract

The chiral benzofuranone structural motif is a prominent feature in many natural products, which exhibit a broad range of biological and pharmaceutical activities. In the past few years, a survey of chiral benzofuranone derivatives based on asymmetric catalysis reveals an increasing number of papers, which reflects the latest achievements to facilitate the synthesis of sufficient quantities of related compounds as potential medicinal agents and biological probes. Recent advances in this area are summarized and classified according to the structure of the starting substrate.

Synthesis of Benzofuranones via Malonates Desymmetrization: Yield Increase by the Portion‐wise Addition of Quinones

“…Their synthesis has not been investigated as intensively as that of the corresponding oxindoles. Some examples of asymmetric synthesis for these compounds start from the pre‐assembled benzofuranone moiety …”

Stereoselective synthesis of diazaspiro[5.5]undecane derivatives via base promoted [5+1] double Michael addition of N,N-dimethylbarbituric acid to diaryliedene acetones

“…In order to access those versatile motifs, there is a need of synthetic strategy for the development of highly efficient methodology. So far, various literature has been documented for the synthesis of spirocycles compounds such as benzofuran spirocyclic (Li et al, 2013(Li et al, , 2014, Spirooxindole (Bencivenni et al, 2009;Chen et al, 2009;Wei and Gong, 2010;Jiang et al, 2010;Chen et al, 2011), spiro cyclohexanone rhodanines (Wu et al, 2012a,b) and spirocyclic azlactones (Weber et al, 2013). Over the last few decades, organocatalysis double Michael reaction of diversified donors with dienones has also been reported for the synthesis of several spirocyclic compounds (Xu et al, 2013;Weber et al, 2013;Fusco and Lattanzi, 2011;Wang et al, 2011;Li et al, 2011;Wu et al, 2011Wu et al, , 2012a.…”

Domino Reaction of Naphthoquinone and β‐Arylpyruvic Acids: Synthesis of 3‐(Naphthoquinonyl)naphthofuran‐2(3H)‐ones

“…Analogous strategies had been reported for reactions of quinones with β‐keto ester derivatives and highly enolizable ketones . Benzo and naphthofuranone skeletons are structural motifs present in many naturally occurring compounds with important biological activities , …”