7622-78-8Relevant articles and documents
A Concise Approach to Oxo-Dehydrorotenoid by Direct Lactonization and the Total Syntheses of Stemonone, Rotenonone, 6-Oxo-dehydroelliptone, and 6-Oxo-6a,12a-dehydrodeguelin
Boonsombat, Jutatip,Thongnest, Sanit,Ruchirawat, Somsak
supporting information, p. 2971 - 2983 (2019/03/27)
An approach to construct the oxo-dehydrorotenoids via direct lactonization of isoflavone-2-carboxylic acids is reported. The present reaction proceeds smoothly with good substrate scope and an operationally simple protocol. The application of this method
β-Deprotonation by Lithium Di-isopropylamide. Vinyl Carbanions from Oxygen Heterocycles in the Synthesis of Carboxylic Acids in the Benzofuran, Flavone, and Coumarin Series and in the Regiospecific Acylation of 2,6-Dimethylchromone
Costa, Ana M. B. S. R. C. S.,Dean, Francis M.,Jones, Michael A.,Smith, Dennis A.,Varma, Rajender S.
, p. 1224 - 1226 (2007/10/02)
Lithium di-isopropylamide at -70 deg C can remove the α-proton from benzofuran in the absence of activating groups and the β-proton if such groups are present; in flavone and 4-methoxycoumarin β-deprotonation occurs readily and the carbanions are easily carboxylated giving acids not previously accessible, while in 2,6-dimethylchromone β-deprotonation is kinetically favoured allowing 3-acylation to be achieved separately from the conventional acylation at the 2-methyl group.