162330-77-0Relevant articles and documents
Regioselective demethylation of 2,6-dimethoxybenzaldehydes with magnesium iodide etherate
Yamaguchi, Seiji,Nedachi, Masahiro,Yokoyama, Hajime,Hirai, Yoshiro
, p. 7363 - 7365 (1999)
Demethylation of asymmetically substituted 2,6-dimethoxybenzaldehydes with magnesium iodide etherate regioselectively single 6-methoxysalicylaldehydes derived from the more unstable chelation.
A new approach to dl-cannabichromene
Yamaguchi,Shouji,Kuroda
, p. 305 - 308 (1995)
Natural dl-cannabichromene was synthesized in 6 steps from methyl 5-methoxy-2-methyl-7-pentyl-2H-chromen-2-acetate prepared by the cyclization of 2-hydroxy-6-methoxy-4-pentylbenzaldehyde with dimethyl isopropylidenemalonate.
7-alkyl-3-benzylcoumarins: A versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists
Rempel, Viktor,Volz, Nicole,Hinz, Sonja,Karcz, Tadeusz,Meliciani, Irene,Nieger, Martin,Wenzel, Wolfgang,Br?se, Stefan,Müller, Christa E.
, p. 7967 - 7977 (2012/11/07)
A series of 7-alkyl-3-benzylcoumarins was designed, synthesized, and tested at cannabinoid CB1 and CB2 receptors in radioligand binding and cAMP accumulation studies. 7-Alkyl-3-benzylcoumarins were found to constitute a versatile scaffold for obtaining potent CB receptor ligands with high potency at either CB1 or CB2 and a broad spectrum of efficacies. Fine-tuning of compound properties was achieved by small modifications of the substitution pattern. The most potent compounds of the present series include 5-methoxy-3-(2-methylbenzyl)-7-pentyl-2H-chromen-2-one (19a, PSB-SB-1201), a selective CB1antagonist (Ki CB 1 0.022 μM), 5-methoxy-3-(2-methoxybenzyl)-7-pentyl-2H-chromen-2- one (21a, PSB-SB-1202), a dual CB1/CB2agonist (CB 1Ki 0.032 μM, EC50 0.056 μM; CB 2Ki 0.049 μM, EC50 0.014 μM), 5-hydroxy-3-(2-hydroxybenzyl)-7-(2-methyloct-2-yl)-2H-chromen-2-one (25b, PSB-SB-1203), a dual CB1/CB2 ligand that blocks CB 1 but activates CB2 receptors (CB1Ki 0.244 μM; CB2Ki 0.210 μM, EC50 0.054 μM), and 7-(1-butylcyclopentyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2- one (27b, PSB-SB-1204), a selective CB2 receptor agonist (CB 1Ki 1.59 μM; CB2Ki 0.068 μM, EC50 0.048 μM).
Experimental and computational studies into an ATPH-Promoted exo-selective IMDA reaction: A short total synthesis of Δ9-THC
Pearson, Emma L.,Kanizaj, Nicholas,Willis, Anthony C.,Paddon-Row, Michael N.,Sherburn, Michael S.
supporting information; experimental part, p. 8280 - 8284 (2010/10/02)
(Figure Presented) Reversal of fortune: The inherent cis stereoselectivity of an intramolecular Diels-Alder reaction is reversed through promotion with aluminum tris(2,6-diphenylphenoxide) (ATPH), allowing a total synthesis of the natural product Δ9
The Diels-Alder approach towards cannabinoids
Lesch, Bernhard,Toraeng, Jakob,Nieger, Martin,Braese, Stefan
, p. 1888 - 1900 (2007/10/03)
Starting from the efficient synthesis of benzopyrans by base-catalyzed condensation reactions between substituted 2-hydroxybenzaldehydes and α,β-unsaturated aldehydes, thermal, Lewis acid catalyzed and enantioselective organo-promoted Diels-Alder reactions towards the tricyclic cannabinoid system are presented. The procedures are exemplified by the synthesis of a pentacycle and various tricycles respectively, in up to 95% enantiomeric excess and provide a versatile entry to this group of natural products with tetrahydrocannabinol (THC) being the most prominent one. Most published strategies are based on the formation of the tricyclic system by condensation between readily available phenols and monoterpenes, whereas we present a novel approach to cannabinoid derivatives based on a modular synthesis. Georg Thieme Verlag Stuttgart.
