SYNTHESIS OF 5',11-DIHYDROXY-DELTA(8)-TETRAHYDROCANNABINOL

Authors
HUFFMAN JW WU MJ BANNER WK DAI D
Citation
Jw. Huffman et al., SYNTHESIS OF 5',11-DIHYDROXY-DELTA(8)-TETRAHYDROCANNABINOL, Tetrahedron, 53(39), 1997, pp. 13295-13306
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
39
Year of publication
1997
Pages
13295 - 13306
Database
ISI
SICI code
0040-4020(1997)53:39<13295:SO5>2.0.ZU;2-X
Abstract
The synthesis of a polar cannabinoid, 5',11-dihydroxy-Delta(8)-tetrahy drocannabinol (2), has been carried out. A key step in the synthesis i s the reaction of an aryllithium derived from 1-(tert-butyldimethylsil yloxy)-5-(3, 5-dimethoxyphenyl)pentane with apoverbenone. Subsequent c onversions provided diol 2, which has significantly less affinity for the cannabinoid receptor than Delta(8)-THC. (C) 1997 Elsevier Science Ltd.