Title: 3,28-Diacetoxylup-20(29)-ene-30-oic Acid and Its ω-Bromoalkyl Esters.
Authors: Ponomaryov, D. V.; Grigorʼeva, L. R.; Nemtarev, A. V.; Tsepaeva, O. V.; Mironov, V. F.; Gnezdilov, O. I.; Antipin, I. S.
Abstract: A convenient procedure has been developed for the synthesis of 3β,28-diacetoxylup-20(29)-en-30-oic acid via oxidation of 3β,28-di-O-acetylbetulin with selenium dioxide in aqueous ethanol on heating, followed by oxidation of 3β,28-diacetoxylup-20(29)-en-30-al thus formed with sodium chlorite in tert-butyl alcohol. The alkylation of 3β,28-diacetoxylup-20(29)-en-30-oic acid with 1,3-dibrompropane and 1,5-dibromopentane in boiling acetonitrile in the presence of potassium carbonate afforded the corresponding ω-bromoalkyl esters in high yields.
Subjects: POTASSIUM carbonate; SELENIUM dioxide; ESTERS; ALKYLATION; ACIDS; ACETONITRILE
Publication: Russian Journal of Organic Chemistry, 2020, Vol 56, Issue 4, p626
ISSN: 1070-4280
Publication type: Academic Journal
DOI: 10.1134/S1070428020040107

3,28-Diacetoxylup-20(29)-ene-30-oic Acid and Its ω-Bromoalkyl Esters.

Ponomaryov, D. V.; Grigorʼeva, L. R.; Nemtarev, A. V.; Tsepaeva, O. V.; Mironov, V. F.; Gnezdilov, O. I.; Antipin, I. S.