Gold-Catalyzed Cyclization of Pyrrole-Tethered Allenynes for the Synthesis of 4-Acylindoles and Its Application to the Ergot Alkaloid Scaffold

Organic Letters 2026 Open access

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Authors: Yusuke Yamamoto, Shinto Takenaka, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno
DOI: 10.1021/acs.orglett.5c05144
Cited by: 0
References: 48

Abstract

Gold-catalyzed cyclization of pyrrole-tethered allenynes produces 4-acylindoles, accompanied by oxidative benzene ring formation. This reaction would proceed via the activation of the allene by a gold catalyst, nucleophilic attack of the alkyne in a 6- endo - dig manner, and trapping of the resulting vinyl cation by an oxygen nucleophile. This methodology was successfully applied to construct the core structure of the ergot alkaloids.

Fields of Study & Subjects

Catalytic Alkyne Reactions Synthesis of Indole Derivatives Organic Chemistry Synthesis Methods

Publication details

Journal / source
Organic Letters
Volume
28
Issue
4
Pages
1331–1336
Publication date
16 January 2026
Language
EN