Enantioselective synthesis of 11-hydroxy-(1 ' S,2 ' R)-dimethylheptyl-Delta(8)-THC, a very potent CB1 agonist

Authors
Liddle, J Huffman, JW
Citation
J. Liddle et Jw. Huffman, Enantioselective synthesis of 11-hydroxy-(1 ' S,2 ' R)-dimethylheptyl-Delta(8)-THC, a very potent CB1 agonist, TETRAHEDRON, 57(36), 2001, pp. 7607-7612
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
36
Year of publication
2001
Pages
7607 - 7612
Database
ISI
SICI code
0040-4020(20010903)57:36<7607:ESO1'S>2.0.ZU;2-A
Abstract
An enantioselective synthesis of the (1S,2R)-dimethylheptyl cannabinoid sid e chain has been developed and employed in the synthesis of 11-hydroxy-(1'S ,2'R)-dimethylheptyl-Delta (8)-THC, one of the most potent traditional cann abinoids known. The synthesis involves a highly stereoselective addition of dimethylcopperlithium to an enoyl sultam which incorporates Opplozer's aux iliary. (C) 2001 Elsevier Science Ltd. All rights reserved.