Synthesis of Novel 8,14-Secoursane Derivatives: Key Intermediates for the Preparation of Chiral Decalin Synthons from Ursolic Acid

Synthesis of Novel 8,14-Secoursane Derivatives: Key Intermediates for the Preparation of Chiral Decalin Synthons from Ursolic Acid

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 acetylatio...

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Veröffentlicht in:Helvetica chimica acta 2012-06, Vol.95 (6), p.1026-1032
Hauptverfasser: Zhang, Chongnan, Yang, Haijun, Lü, Guangying, Liu, Cailin, Tang, Yun, Liu, Laibao
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Sprache:eng
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14-Secoursane
8,14‐Secoursane
Ring opening
Ursolic acid
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container_issue 6
container_start_page 1026
container_title Helvetica chimica acta
container_volume 95
creator Zhang, Chongnan
Yang, Haijun
Lü, Guangying
Liu, Cailin
Tang, Yun
Liu, Laibao
description 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.
doi_str_mv 10.1002/hlca.201100452
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subjects 14-Secoursane
8,14‐Secoursane
Ring opening
Ursolic acid
title Synthesis of Novel 8,14-Secoursane Derivatives: Key Intermediates for the Preparation of Chiral Decalin Synthons from Ursolic Acid
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