Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 0, 1982
Previous Article Next Article

Dihydrostilbenes of Cannabis. Synthesis of canniprene

Abstract

Canniprene (10) is synthesised via reaction of a phenolate-anion ylide with a benzyl-protected aldehyde. Benzoylation, followed by hydrogenation and hydrogenolysis of the resulting stilbene, leads to a half-benzoylated bibenzyl which is converted into its O-dimethylprop-2-ynyl derivative. Semi-hydrogenation, Claisen rearrangement, and debenzoylation gives canniprene. In a second synthesis the prenylated (3-methylbut-2-enylated) and benzyl-protected ring-B section is made first and converted by Wittig reaction into a dibenzyl-protected stilbene. The stilbene is reduced and the benzyl groups removed in one step, without affecting the prenyl group, by sodium in butanol: magnesium in methanol is capable of stilbene reduction without debenzylation. This practical synthesis proceeds in 19% overall yield from the dimethylprop-2-ynyl ether of isovanillin (14) and is applicable to isotope-labelling. The use of p-bromophenacyl (PBP) ether and methoxyethoxymethyl (MEM) ether protection as the basis for canniprene synthesis is also considered.

Other bibenzyls relevant to the natural products of Cannabis are made and the methylated chroman (37) derived from canniprene is also synthesised.

Back to tab navigation

Article information


J. Chem. Soc., Perkin Trans. 1, 1982, 1467-1475
Article type
Paper

Dihydrostilbenes of Cannabis. Synthesis of canniprene

L. Crombie and S. V. Jamieson, J. Chem. Soc., Perkin Trans. 1, 1982, 1467
DOI: 10.1039/P19820001467

Search articles by author

Spotlight

Advertisements