STEREOSELECTIVE SYNTHESIS OF THE EPIMERIC DELTA(7)-TETRAHYDROCANNABINOLS

被引：12

作者：

HUFFMAN, JW

BANNER, WK

ZOOROB, GK

JOYNER, HH

REGGIO, PH

MARTIN, BR

COMPTON, DR

机构：

[1] KENNESAW STATE COLL,DEPT CHEM,MARIETTA,GA 30061

[2] VIRGINIA COMMONWEALTH UNIV,MED COLL VIRGINIA,DEPT PHARMACOL & TOXICOL,RICHMOND,VA 23298

来源：

TETRAHEDRON | 1995年 / 51卷 / 04期

关键词：

D O I：

10.1016/0040-4020(94)00995-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Roth C9 epimers of Delta(7)-THC (3 and 4) have been synthesized from Delta(8)-THC methyl ether (12). Hydroboration of 12 gave a mixture of stereoisomeric 8-hydroxyhexahydrocannabinols. The 8 alpha-ol was converted into the 9 beta-methyl epimer (4) of Delta(7)-THC, while the 8 beta-ol was converted into 3. Molecular modeling indicated that 4 should have significant cannabinoid activity, while 3 was predicted to he weakly active. These predictions were borne out by both in vitro and in vivo pharmacology.

引用

页码：1017 / 1032

页数：16

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