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

Chemistry of the Podocarpaceae. XXIV. Ring-A modifications of Abieta- 8,11,13-trien-18-oic acid

RC Cambie and RA Franich

Australian Journal of Chemistry 23(1) 93 - 105
Published: 1970

Abstract

A convenient route from abieta-8,11,13-trien-18-oic acid (10) to abieta5,8,11,13-tetraen-3-one (27) has been developed involving selective epoxidation of the alkene mixture (2) obtained by oxidative decarboxylation of the acid with lead tetraacetate. Treatment of the 3a,4a-epoxide (9) with lithium diethylamide gives a quantitative yield of the allylic alcohol (19). Brief treatment of this allylic alcohol with N-lithioethylenediamine gives the α, β-unsaturated alcohol (25), which on oxidation affords the enone (24). Methylation of the latter compound with methyl iodide and potassium t-butoxide in t-butanol yields abieta-5,8,11,13-tetraen-3-one (27) in 43% overall yield from the alkene mixture (2). Other reactions of the 3α, 4α-epoxide (9) are reported and discussed.

https://doi.org/10.1071/CH9700093

© CSIRO 1970

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