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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. XLIX. Isomerization of 12-Methoxy-19-norpodocarpatetraenes

RC Cambie, BA Grigor, RC Hayward and AJ Nielson

Australian Journal of Chemistry 27(9) 2017 - 2024
Published: 1974

Abstract

Methods for isomerization of the 12-methoxy-19-norpodocarpatetraene mixture obtained from oxidative decarboxylation of 12-methoxypodocarpa-8,11,13-trien-19-oic acid (1) with lead tetraacetate have been examined. Acid-catalysed isomerization gives a mixture of the endocyclic isomers (11) and (19) while iodine-catalysed isomerization gives a mixture enriched in the isomer (19) to the extent of 80%. Metal-catalysed decarbonylation of the acid chloride (6) and oxidative decarboxylation of the acetoxy acid (7) have also been examined.

https://doi.org/10.1071/CH9742017

© CSIRO 1974

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