1384247-09-9Relevant articles and documents
Synthesis of novel 8,14-secoursane derivatives: Key intermediates for the preparation of chiral decalin synthons from ursolic acid
Zhang, Chongnan,Yang, Haijun,Lue, Guangying,Liu, Cailin,Tang, Yun,Liu, Laibao
, p. 1026 - 1032 (2012/08/08)
The novel 8,14-secoursatriene derivative 6 was synthesized starting from ursolic acid (1) via methyl esterification of the 17-carboxylic acid group and benzoylation of the 3-hydroxy group (→ 2; Scheme 1), ozone oxidation of the C(12)=C(13) bond (→ 3), dehydrogenation with Br2/HBr (→ 4), enol acetylation of the resulting carbonyl group (→ 5; Scheme 2), and ring-C opening with the aid of UV light (→ 6). Ring-C-opened dienone derivative 7 of ursolic acid was also obtained via selective hydrolysis of 6 (Scheme 2). Both compounds 6 and 7 are key intermediates for the preparation of chiral decalin synthons from ursolic acid.