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A Synthesis of the Phenolic Lipid, 3-[(Z)-pentadec-8-enyl] Catechol, (15:1)-urushiol

A Synthesis of the Phenolic Lipid, 3-[(Z)-pentadec-8-enyl] Catechol, (15:1)-urushiol

John H P Tyman, Brian G Schofield, Choong H Khor

Chem Phys Lipids. 2002 Dec;120(1-2):101-8.

PMID: 12426079

Abstract:

A synthesis of (15:1)-urushiol, urushiol monoene, 3-[(Z)-pentadec-8-enyl] catechol, 1,2-dihydroxy-3-[(Z)-pentadec-8-enyl] benzene, one of the toxic principles of Rhus toxicodendron and of Rhus vernicifera is described. 6-Chlorohexan-1-ol protected at the OH group with ethyl vinyl ether reacted with 2,3-dimethoxybenzaldehyde in the presence of lithium to give, after removal of the protective group with methanolic 4-toluenesulphonic acid, 1-(2,3-dimethoxyphenyl) heptane-1,7-diol. Catalytic hydrogenolysis in ethanol with palladium-carbon selectively afforded 7-(2,3-dimethoxyphenyl)heptane-1-ol accompanied by a small proportion of the 7-(3-methoxyphenyl)heptane-1-diol, formed by demethoxylation. Reaction of the dimethoxy compound with boron tribromide resulted in both bromination and demethylation to give 7-(2,3-dihydroxyphenyl) heptylbromide. This bromide in tetrahydrofuran (THF) containing hexamethylphosphoric triamide reacted with excess lithium oct-1-yne to give 3-(pentadec-8-enyl)catechol which, by catalytic hydrogenation in ethyl acetate containing quinoline, selectively formed the required cis product, 3-[(Z)-pentadec-8-enyl]catechol which was identical chromatographically and spectroscopically with urushiol monoene separated from the natural product.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP35237026	Urushiol (15:1)		35237-02-6	Price
AP83543377	Urushiol (15:3)		83543-37-7	Price

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