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Unsaturated acids, including difficultly accessible ceanothane-type ones, were prepared via alkaline hydrolysis of semi-synthetic triterpenoids with 1-cyano- or 3-methyl-1-cyanoalkene fragments in five-membered ring A. Regioselective reduction of 1-cyano-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene by DIBAL-H… Click to show full abstract
Unsaturated acids, including difficultly accessible ceanothane-type ones, were prepared via alkaline hydrolysis of semi-synthetic triterpenoids with 1-cyano- or 3-methyl-1-cyanoalkene fragments in five-membered ring A. Regioselective reduction of 1-cyano-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene by DIBAL-H synthesized 2-aminomethyl-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene. The synthesized triterpene derivatives possessed virucidal activity against herpes simplex virus type 1 (HSV-1) according to screening for inhibitory and virucidal activity. Methyl ceanotha-1(3),20(30)-dien-2,28-dioic acid 5 (ET50 28.3 min) and its 3-methyl derivative 7 (ET50 17.7 min) were the most active compounds.
Journal Title: Chemistry of Natural Compounds
Year Published: 2017
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