90679-16-6Relevant academic research and scientific papers
Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid
Beaudry, Christopher M.,Points, Gary L.,Stout, Kenneth T.
, p. 16655 - 16658 (2020)
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.
