SYNTHESIS OF URUSHENOL, THE MONO-OLEFINIC COMPONENT OF THE ALLERGENIC PRINCIPLES OF POISON IVY AND JAPANESE LAC
SYNTHESIS OF URUSHENOL, THE MONO-OLEFINIC COMPONENT OF THE ALLERGENIC PRINCIPLES OF POISON IVY AND JAPANESE LAC
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DOI：
10.1021/jo01089a025
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发表时间：
1959-01-01
影响因子：
3.6
通讯作者：
DAWSON, CR
中科院分区：
文献类型：
--
作者：
LOEV, B;DAWSON, CR
漆酚的合成首次为临床研究提供了一种烯属儿茶酚，该烯属儿茶酚构成了毒葛和日本紫胶的过敏原。邻苯二酚羟基在烯烃侧链的构建期间通过苄基化保护。苄基醚随后裂解，并且苯乙烯型双键同时通过钠和丁醇还原。所需的8烯键在还原裂解期间不改变。该方法适用于毒葛漆酚高级烯烃的合成。
The synthesis of urushenol has made available for clinical study for the first time one of the olefinic catechols that make up the allergenic principle of poison ivy and Japanese lac. The catechol hydroxyl groups are protected by benzylation during the construction of the olefinic side chain. The benzyl ethers are subsequently cleaved, and a double bond of the styrene type is simultaneously reduced, by means of sodium and butanol. The desired 8 olefinic bond is not altered during the reductive cleavage. It is believed that the method will be adaptable to the synthesis of the higher olefinic components of poison ivy urushiol.