83638-28-2Relevant academic research and scientific papers
1,2-Disubstituted Ethanes As Possible Precursors For The Synthesis of Cannabis Spirans
Crombie, Leslie,Crombie, W. Mary L.,Jamieson, Sally V.,Tuchinda Patoomratana,Whitaker, Alison J.
, p. 1485 - 1492 (2007/10/02)
Three possible methods for converting suitable 1,2-disubstituted ethanes into Cannabis spirans have been investigated. 4',5-Dihydroxy-3-methoxybibenzyl underwent intramolecular o-p- and p-p-coupling with ferricyanide in a chloroform-aqueous potassium carbonate system, but yields were low: certain other oxidants did not succeed or gave only traces of product.A method for making 1-hydroxy-1-(3,5-dimethoxyphenylethyl)cyclohexan-4-one ethylene acetal or thioacetal via a Birch reaction is described: despite favourable precedent, acid-catalysed cyclisation led to octahydrophenanthrenones rather than spiro-ketones, whilst N,N-dimethylformamide dineopentyl acetal gave two olefins.Jacquesy's super-asid method for making spirocyclohexenones from a methoxylated bibenzyl was not applicable to the 3,4',5-trimethoxy-case, which would have given cannabispirenone methyl ether, presumably because of protonation of both aromatic systems.
Studies on Reductive Alkylation. A Highly Efficient Synthesis of the Phytoalexin Orchinol
Gunter, Maxwell J.,Mander, Lewis N.
, p. 675 - 678 (2007/10/02)
Reductive alkylation of 2,5-dimethoxybenzoic acid (1) with 2-(3',5'-dimethoxyphenyl)ethyl iodide (2) followed by cyclodehydration and oxidative decarboxylation afforded orchinol (5) in high overall yield.A simple synthesis of iodide (2) based on the reduc
