Affiliation:
1. Ufa Institute of Chemistry - Subdivision of the Ufa Federal Research Centre of the Russian Academy of Sciences
Abstract
The review describes the low-temperature reduction of (-)-mentholactone with diisobutylaluminum hydride in methylene chloride studied by the authors. It was found that, depending on the reaction conditions, it proceeds with the formation of three products: 7 S -isopropyl-4 R -methyloxepan-2 S -ol [(-)-mentholactol], 8-hydroxy-2,6 R -dimethyloctan-3-one or 2 S -isobutoxy-7 S -isopropyl-4 R -methyloxepane, for each of which the probable routes are given and the conditions for selective formation are selected. A new reaction in the chemistry of organoaluminum compounds has been discovered - the formation of isobutyl acetals of 2-oxepanols during low-temperature (-70°C) reduction of 7-membered lactones with two-fold or more molar amounts of diisobutylaluminum hydride in methylene chloride. On the basis of (-)-mentholactol, its aluminate, and 8-hydroxy-2,6R-dimethyloctan-3-one, a number of low molecular weight bioregulators, including optically active pheromones of insect pests in agriculture and forestry, have been synthesized.
Publisher
The Russian Academy of Sciences
Reference80 articles.
1. Яковлева М.П., Денисова К.С., Выдрина В.А., Толстиков А.Г., Ишмуратов Г.Ю. ЖОрХ. 2021, 57, 607-660.
2. Methods for Macrolactonization of Seco Acids in the Synthesis of Natural and Biologically Active Compounds
3. Macrolactonizations in the Total Synthesis of Natural Products
4. Oxygen insertion reactions of bridged bicyclic ketones
5. Ишмуратов Г.Ю., Выдрина В.А., Галкина Ю.А., Яковлева М.П., Ишмуратова Н.М., Толстиков А.Г. ХПС. 2015, 871-892.