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Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid
Author(s) -
Points Gary L.,
Stout Kenneth T.,
Beaudry Christopher M.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004107
Subject(s) - regioselectivity , lysergic acid , intramolecular force , chemistry , cycloaddition , alkyne , yield (engineering) , substitution (logic) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , computer science , programming language , materials science , metallurgy
A Diels–Alder reaction‐based strategy for the synthesis of indoles and related heterocycles is reported. An intramolecular cycloaddition of alkyne‐tethered 3‐aminopyrones gives 4‐substituted indolines in good yield and with complete regioselectivity. Additional substitution is readily tolerated in the transformation, allowing synthesis of complex and non‐canonical substitution patterns. Oxidative conditions give the corresponding indoles. The strategy also allows the synthesis of carbazoles. The method was showcased in a formal synthesis of lysergic acid.