Synthesis of 3- and 4-(ω-Phenylalkyl)catechols, the Sap Exuded from a Burmese Lac Tree, Melanorrhoea Usitate
The presence of 3- and 4-(ω-phenylalkyl)catechols in Burmese lac has been confirmed by their synthesis. 3-(ω-Phenylalkyl)veratroles were synthesized by alkylation of ω-phenylalkyl bromide with aryl lithium derived from veratrole. 4-(ω-phenylalkyl)veratroles were similarly obtained from w-phenylalkyl bromide and 4-bromoveratrole.Demethylation of 3- and 4-(ω-phenylalkyl)veratroles with boron tribromide gave the corresponding catechols in good yields.
Miyakoshi, Tetsuo,Du, Yumin,Kumanotani, Ju
p. 1054 - 1056
(2007/10/02)
Synthesis of 3-(ω-Phenylalkyl)catechols, Phenolic Lipids found in Sap of the Burmese Lac Tree, via Directed Metallation
3-(ω-Phenylalkyl)catechols were synthesized via directed metallation.