Process for the preparation of (R) - (+) - (gamma) - jasmolactona and (R) - (+) - (gamma) - jasmolactona thus obtained

摘要

Process for the preparation of (R) - (+) - (sym) - jasmolactona and (R) - (+) - (sym) - jasmolactona thus obtained.It is a compound possessing interesting organoleptic properties and is used in the food industry and perfumery.This compound is known as one of the main components present in the oil of jasmine and, together with the jasmona and methyl jasmonato,It is described as one of the main responsible for the odor observed in essential oil extracted from the flowers of jasmine.Process for preparation of (R) - (+) - (sym) - jasmolactona involves five steps reacionais on the acid 4 - cetopimu00e9lico commercial and employs a lactonizau00e7u00e3o promoted by pancreatic lipase enzymePig (PPL) in the stage of dessimetrizau00e7u00e3o.More specifically,The process is characterized by the selective reduction of S - (+) - 3 - (5 '- hydroxy - 2 - tetrahydro furanil) propanoate benzila R - (+) - 3 - (5 - hidroxitetrahidro - 2 - furanil) propanoate with hydride benzila Di is.Obutil aluminium (DIBAL - H), followed by a Wittig reaction of the type between the lactol (R) - (VI) and two equivalents of propilidenotrifenilfosforana,Generated by reaction of propiltrifenilfosfu00f3nio bromide with sodium hydride in dimethyl sulfoxide (DMSO),Taking the (R) - (sym) - jasmolactona between 80 and 82% of income as a mixture 89: 11 isomers, Z: and determined by gas chromatography.