264. Cannabis indica. Part V. The synthesis of cannabinol

Reagent‐Controlled Cyclization–Deprotection Reaction to Yield either Fluorenes or Benzochromenes

“…6 H ‐Benzo[ c ]chromenes, e.g., 6,6‐dimethyl‐6 H ‐benzo[ c ]chromene ( 1 ), with various biological activities are abundant in nature. Examples include the antiprotozoal pulchrol ( 2 ),1 the antibacterial didehydroconicol ( 3 ),2 and the psychotropic cannabinol ( 4 ) 3. 9 H ‐Fluorene ( 5 )4 is a member of the polycyclic aromatic hydrocarbon (PAH) family, and some fluorenes such as 6 5 are carcinogens.…”

Isolation of two benzocoumarins from ‘clover stone’ a type of renal calculus found in sheep

“…The correctness of his assignment of structure is supported by the lack of a positive indophenol reaction and by the identity of the methyl ether of his product with the product of oxidation of the corresponding dibenzopyran (Cavill et al 1958). Further, Hey et al (1963) showed that the benzocoumarin, arising from the acid-catalysed rearrangement of the dienone (II), was identical with that made by Ghosh, Todd & Wilkinson (1940) to which structure (I; R = H; R' = OH) had been given. It is evident that only one benzocoumarin structure could be formed in both these synthetic routes, namely structure (I; R = H; R' = OH).…”

Pharmacological and therapeutic secrets of plant and brain (endo)cannabinoids

“…Several years later, Todd's group and independently Adam's group elucidated the correct structure of the first natural cannabinoid, CBN. [46][47][48] Subsequently, the second Cannabis constituent, cannabidiol (CBD) was isolated, but its structure was only partially elucidated. 49 Synthetic tetrahydrocannabinol (THC) derivatives were prepared that showed Cannabis-like activity in animal tests.…”

“…249 The ability of dimethylheptyl analogues of 2-AG and noladin ether (46)(47)(48)(49)(50) to activate the CB 1 receptor were not improved by replacement of the terminal pentyl chain with the dimethylheptyl one. 250 To improve enzymatic stability of 2-AG, a-methylated analogues (51a, 51b) of this endocannabinoid were synthesized.…”