Stereoselective synthesis of the epimeric Δ7-tetrahydrocannabinols

Autor:	Grace K. Zoorob, John W. Huffman, Patricia H. Reggio, H. Howard Joyner, W. Kenneth Banner, Billy R. Martin, David R. Compton
Rok vydání:	1995
Předmět:	Molecular model Stereochemistry Chemistry medicine.medical_treatment Organic Chemistry Ether Biochemistry In vitro Hydroboration chemistry.chemical_compound In vivo Drug Discovery medicine Organic chemistry Stereoselectivity Epimer Cannabinoid
Zdroj:	Tetrahedron. 51:1017-1032
ISSN:	0040-4020
Popis:	Both C9 epimers of Δ7-THC (3 and 4) have been synthesized from Δ8-THC methyl ether (12). Hydroboration of 12 gave a mixture of stereoisomeric 8-hydroxyhexahydrocannabinols. The 8α-ol was converted into the 9β-methyl epimer (4) of Δ7-THC, while the 8β-ol was converted into 3. Molecular modeling indicated that 4 should have significant cannabinoid activity, while 3 was predicted to be weakly active. These predictions were borne out by both in vitro and in vivo pharmacology.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8bf00f2601634426c714b2b0c9d28bcb https://doi.org/10.1016/0040-4020(94)00995-7 Zobrazit plný text záznamu Full Text from ScienceDirect