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

Constituents of Eupomatia species. The structure and synthesis of eupomatene, a lignan of novel type from Eupomatia laurina R. Br

RS McCredie, E Ritchie and WC Taylor

Australian Journal of Chemistry 22(5) 1011 - 1032
Published: 1969

Abstract

The bark of Eupomatia laurina R. Br. yielded the known alkaloid, liriodenine, and four new substances. One of these, eupomatene, was shown by degradation to be 7-methoxy-3-methyl-2-(3?,4?- methylenedioxyphenyl)-5-trans-propenylbenzofuran. The dihydro derivative and eupomatene itself were synthesized. It is proposed that the term ?lignan? be extended to cover all natural products of low molecular weight that arise primarily from the oxidative coupling of p- hydroxyphenylpropene units and that eupomatene be then classified as a lignan.     A chlorotropolone has been isolated from a Reimer-Tiemann reaction on a simple phenol.

https://doi.org/10.1071/CH9691011

© CSIRO 1969

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