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The synthesis of hexahydro‐6 H ‐dibenzo[ b,d ]pyrans: Derivatives of 9‐Nor‐9β‐hydroxyhexahydrocannabinol
Author(s) -
Melvin Lawrence S.,
Bordner Jon,
Hada William A.,
Johnson M. Ross
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270312
Subject(s) - chemistry , stereochemistry , phenol , crystal structure , medicinal chemistry , organic chemistry
To assess the importance of the phenol functionality in cannabinoids for analgetic activity a new series of 9‐nor‐9β‐hydroxyhexahydrocannabinoids was prepared. The synthesis of 1‐substituted (H, CH 2 OH, OH, NH 2 ) 6aβ,7,8,9,10,10a α ‐hexahydro‐9β‐hydroxy‐6,6‐dimethyl‐3‐[1‐methyl‐4‐phenylbutoxy]‐6 H ‐dibenzo[ b,d ]pyrans from 3,5‐dihydroxystilbene, 3,3′,5,5′‐tetrahydroxystilbene or 1,3,5‐trihydroxybenzene is described. Relative stereochemistry and structure confirmations were obtained by nmr and X‐ray crystal analysis.