A FACILE SYNTHESIS OF 9-NOR-9-HYDROXYHEXAHYDROCANNABINOL VIA INTRAMOLECULAR REVERSE ELECTRON DEMAND DIELS-ALDER CYCLIZATION
A simple and efficient new synthesis of 9-nor-9-hydroxyhexahydrocannabinol is achieved, through the intramolecular cycloaddition of an o-quinonemethide which is generated from 2-(1-hydroxy-3-methoxymethoxy-7-methyl-6-octenyl)-1,3-bis(O-methoxymethyl)olivetol (12b), which in turn is prepared by reaction of the lithiated olivetol bis(methoxymethyl)ether with 3-methoxymethoxy-7-methyl-6-octenal (9).
Lu, Zhan Guo,Inoue, Seiichi
p. 1107 - 1117
(2007/10/02)
9 Nor 9 hydroxyhexahydrocannabinols. Synthesis, some behavioral and analgesic properties, and comparison with the tetrahydrocannabinols
The racemic mixture and levo isomer of both 9 nor 9α hydroxyhexahydrocannabinol and its 9β hydroxy isomer were prepared. Both α and β hydroxy compounds were active in the dog ataxia test and depressed spontaneous activity in mice. However, only the β hydr
Wilson,May,Martin,Dewey
p. 1165 - 1167
(2007/10/18)
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