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Synthesis of Novel 8,14‐Secoursane Derivatives: Key Intermediates for the Preparation of Chiral Decalin Synthons from Ursolic Acid
Author(s) -
Zhang Chongnan,
Yang Haijun,
Lü Guangying,
Liu Cailin,
Tang Yun,
Liu Laibao
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100452
Subject(s) - chemistry , ursolic acid , synthon , ring (chemistry) , derivative (finance) , decalin , hydrolysis , dehydrogenation , organic chemistry , enol , stereochemistry , medicinal chemistry , catalysis , chromatography , financial economics , economics
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 Br 2 /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.