This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.
847-86-9Relevant articles and documents
Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (?)-Thebainone A
Hou, Si-Hua,Prichina, Adriana Y.,Dong, Guangbin
, p. 13057 - 13064 (2021)
Herein, we describe the development of a deconstructive strategy for the first asymmetric synthesis of (?)-thebainone A, capitalizing on an enantioselective C?C bond activation and a C?O bond cleavage reaction. The rhodium-catalyzed asymmetric “cut-and-sew” transformation between sterically hindered trisubstituted alkenes and benzocyclobutenones allowed efficient construction of the fused A/B/C rings and the quaternary center of the natural product. The newly optimized conditions show broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). Taking advantage of boron-mediated ether bond cleavage, we completed the synthesis of the morphine alkaloid (?)-thebainone A by two complementary routes.
-
Bentley,Wain
, p. 972,974 (1952)
-
Synthesis and pharmacological evaluation of aminothiazolomorphinans at the Mu and Kappa opioid receptors
Provencher, Brian A.,Sromek, Anna W.,Li, Wei,Russell, Shayla,Chartoff, Elena,Knapp, Brian I.,Bidlack, Jean M.,Neumeyer, John L.
, p. 8872 - 8878 (2013/12/04)
Previous studies with aminothiazolomorphinans suggested that this class of opioid ligands may be useful as a potential pharmacotherapeutic to decrease drug abuse. Novel aminothiazole derivatives of cyclorphan were prepared to evaluate a series of aminothiazolomorphinans with varying pharmacological properties at the κ opioid receptor (KOR) and μ opioid receptor (MOR). This study was focused on exploring the regioisomeric analogs with the aminothiazole on the C-ring of the morphinan skeleton. Receptor binding and [35S] GTPγS binding assays were used to characterize the affinity and pharmacological properties of the aminothiazolomorphinans. Intracranial self-stimulation (ICSS) was used to compare the effects of a representative aminothiazolomorphinan with the morphinan mixed-KOR/MOR agonist butorphan (MCL-101) on brain-stimulation reward.
One-pot conversion of thebaine to hydrocodone and synthesis of neopinone ketal
Carroll, Robert J.,Leisch, Hannes,Rochon, Lena,Hudlicky, Tomas,Cox, D. Phillip
experimental part, p. 747 - 752 (2009/07/25)
The ethylene glycol ketal of neopinone was prepared in a one-pot procedure by the reaction of thebaine with ethylene glyocol in the presence of p-toluenesulfonic acid. The ketal is also an intermediate in the conversion of thebaine to hydrocodone with ethylene glycol and Pd(OAc)2, followed by hydrogenation. Additionally, a one-pot procedure for the conversion of thebaine to hydrocodone was achieved by employing palladium catalysis in aqueous medium. Palladium serves a dual purpose in this transformation, first for the activation of the dienol ether of thebaine and second as a hydrogenation catalyst. This procedure was found to be comparable to the two-step protocol which employs diimide reduction of thebaine followed by acid-catalyzed hydrolysis of the resulting 8,14-dihydrothebaine to hydrocodone. Experimental and spectral data are provided for all compounds.