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Access to γ-Carbolines: Synthesis of Isocryptolepine. | LitMetric

Access to γ-Carbolines: Synthesis of Isocryptolepine.

J Org Chem

Department of Applied Biological Sciences, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuencho, Nakaku, Sakai, Osaka 599-8531, Japan.

Published: December 2021

A new method to synthesize γ-carboline derivatives has been developed starting from 3,5-dibromo-4-pyridinamine by monoarylation using the Suzuki-Miyaura cross-coupling reaction followed by the base-mediated ring closure to pyrrole formation. Synthesis of a series of γ-carboline derivations from the 4-brominated γ-carboline has been achieved by employing various coupling reactions and N-alkylations. This method has been applied for the synthesis of the antimalarial and anticancer natural product isocryptolepine. The photophysical properties of novel γ-carboline derivations are also reported.

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Source
http://dx.doi.org/10.1021/acs.joc.1c02026DOI Listing

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