Patent ID: 6150538
Filing Date: 2000-11-21
Classification: C07D

Abstract:
A process for manufacturing cis-isoambrettolide comprising:(a) providing trans-16-hydroxy-9-hexadecenoic acid or acid ester having the formula: ##STR4## wherein R.sup.1 is selected from the group consisting of hydrogen and an acetyl radical and R.sup.2 is selected from the group consisting of hydrogen and a methyl radical;(b) contacting said acid or acid ester with a mixture of a peroxide and a carboxylic acid to form the epoxide of the said acid or acid ester;(c) subjecting said epoxide to hydrolysis in the presence of an acidic or basic medium to form erythro-aleuritic acid or acid ester;(d) heating said acid or acid ester in the presence of an ortho ester having the formula HC(OR.sup.3).sub.3, where R.sup.3 is selected from the group consisting of a methyl and ethyl radical, to form the dioxolane;(e) subjecting said dioxolane to pyrolysis treatment in the presence or absence of organic solvent to form cis-16-hydroxyhexadecenoic acid or acid ester having the formula: ##STR5## and, (f) subjecting the acid or acid ester product from step (e) to macrolactonization conditions.