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Photocatalytic enantioselective Minisci reaction of β-carbolines and application to natural product synthesis

Mupeng Luo, Yi‐Jie Gu, Shouguo Wang

2022Chemical Science28 citationsDOIOpen Access PDF

Abstract

a Minisci-type radical process under a photo-redox and chiral phosphoric acid cooperative catalytic system has been disclosed. Through this protocol, a wide range of C1 aminoalkylated β-carbolines were constructed directly with high levels of enantioselectivities from readily available β-carbolines and alanine-derived redox-active esters. This transformation allows straightforward access to highly valuable enantioenriched β-carbolines, which are an intriguing structural motif in valuable natural products and synthetic bio-active compounds. This protocol has been utilized as a highly efficient synthetic strategy for the concise asymmetric total synthesis of marine alkaloids eudistomin X, (+)-eudistomidin B and (+)-eudistomidin I.

Topics & Concepts

Enantioselective synthesisPhotocatalysisNatural productChemistryCombinatorial chemistryNatural (archaeology)Product (mathematics)CatalysisOrganic chemistryMathematicsGeographyArchaeologyGeometrySynthesis of Indole DerivativesSynthesis and bioactivity of alkaloidsAsymmetric Synthesis and Catalysis