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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

22b-[(S)-2-Methylbutanoyloxy]-3-oxoolean-12-en-28-oic acid, a new constituent of Lantana camara

SR Johns, JA Lamberton, TC Morton, H Suares and RI Willing

Australian Journal of Chemistry 36(9) 1895 - 1902
Published: 1983

Abstract

22β-[(S)-2-Methylbutanoyloxy]-3-oxoolean-12-en-28-oic acid, a new constituent of Lantanu camara L. is closely related to lantadene A and lantadene B. Although hydrolysis gives 2-methylbutanoic acid as a partial racemate, it has been shown by n.m.r. spectroscopy that the natural ester is theoptically pure (S)-isomer. Catalytic hydrogenation of lantadene A gives a mixture of diastereoisomeric esters in which the (S)-2-methylbutanoate predominates, and a 1 : 1 mixture of the (R)- and(S)-esters was obtained by esterification with (RS)-2-methylbutanoyl chloride of 22β-hydroxy-3-oxoolean-12-en-28-oic acid protected as the diphenylmethyl ester.

https://doi.org/10.1071/CH9831895

© CSIRO 1983

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