Intramolecular Fischer Indole Synthesis for the Direct Synthesis of 3,4-Fused Tricyclic Indole and Application to the Total Synthesis of (−)-Aurantioclavine

Aryl hydrazides with a ketone or aldehyde containing side chains linked to the meta-position of the aromatic ring undergo acid-promoted intramolecular Fischer indole synthesis to generate 3,4-fused tricyclic indoles. The preparative utility of this conceptually new synthetic approach, which does not...

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Bibliographic Details
Published in:Organic letters 2016-10, Vol.18 (19), p.5098-5101
Main Authors: Park, Jun, Kim, Dong-Hyun, Das, Tapas, Cho, Cheon-Gyu
Format: Article
Language:English
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Summary:Aryl hydrazides with a ketone or aldehyde containing side chains linked to the meta-position of the aromatic ring undergo acid-promoted intramolecular Fischer indole synthesis to generate 3,4-fused tricyclic indoles. The preparative utility of this conceptually new synthetic approach, which does not require prefunctionalization of the indole ring, was demonstrated by its application to a concise total synthesis of (−)-aurantioclavine.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02541