Synthesis of Polycyclic Indolines by Utilizing a Reduction/Cyclization Cascade Reaction

European journal of organic chemistry 2021(45), 6097-6101 (2021). doi:10.1002/ejoc.202101191

Synthesis of Polycyclic Indolines utilizing a reduction/cyclization cascade reaction

Subsequent reduction and dearomatizing cyclization reactions open up an entry into the synthesis of novel N-fused polycyclic indolines. The dearomatizing cyclization as key step of the sequence proceeds well with Cu(OTf)2 or TfOH as catalyst. At elevated temperature reduction of nitro-substituted precursors with iron under acidic conditions affords a broad variety of polycyclic indolines directly in a two-step cascade reaction in good to excellent yields. Using the developed protocol, the alkaloids Tryptanthrin and Phaitanthrin C have been prepared. peerReviewed

Cover Feature: Synthesis of Polycyclic Indolines by Utilizing a Reduction/Cyclization Cascade Reaction (Eur. J. Org. Chem. 45/2021)

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