67175-79-5Relevant academic research and scientific papers
Synthesis and pharmacological evaluation of dhβe analogues as neuronal nicotinic acetylcholine receptor antagonists
Jepsen, Tue Heesgaard,Jensen, Anders A.,Lund, Mads Henrik,Glibstrup, Emil,Kristensen, Jesper Langgaard
, p. 766 - 770 (2014)
Dihydro-β-erythroidine (DHβE) is a member of the Erythrina family of alkaloids and a potent competitive antagonist of the α4β2-subtype of the nicotinic acetylcholine receptors (nAChRs). Guided by an X-ray structure of DHβE in complex with an ACh binding p
The Pummerer Cyclization Route to the Ibophyllidine Alkaloids. Total Synthesis of (+/-)-Deethylibophyllidine
Catena, Juanlo,Valls, Nativitat,Bosch, Joan,Bonjoch, Josep
, p. 4433 - 4436 (1994)
Pummerer cyclization of β-aminoethyl sulfoxide 6 was effectively achieved using TFAA-TFA in toluene at 80 deg C.The cyclized product 7 was then converted to the alkaloid deethylibophyllidine.The required pyrrolocarbazole 6 was prepared in five steps from 4-methoxyphenethylamine.
An Efficient Palladium Mediated Synthesis of (±)-γ-Lycorane
Shao, Zhihui,Chen, Jingbo,Huang, Rong,Wang, Chenying,Li, Liang,Zhang, Hongbin
, p. 2228 - 2230 (2007/10/03)
An intramolecular approach incorporating a Michael addition followed by a palladium-mediated arylation of ketone towards the synthesis of Amaryllidaceae alkaloid (±)-γ-lycorane was reported.
Synthesis of cationic 1-substituted-dicarbonyl(η5-4- methoxycyclohexadienyl)-(triphenylphosphine)iron complexes
Guillou, Catherine,Millot, Nicolas,Reboul, Vincent,Thal, Claude
, p. 4515 - 4518 (2007/10/03)
Cationic 1-substituted-dicarbonyl(π5-4-methoxycyclohexadienyl)- (triphenylphosphine)iron complexes 10 form a new class of highly functionalised iron complexes which have never been described. They were obtained from neutral 1-substituted (πsup
Total synthesis of (±)-deethylibophyllidine: Studies of a Fischer indolization route and a successful approach via a Pummerer rearrangement/thionium ion-mediated indole cyclization
Bonjoch, Josep,Catena, Juanlo,Valls, Nativitat
, p. 7106 - 7115 (2007/10/03)
The total synthesis of (±)-deethylibophyllidine is described, proceeding in eight steps from 4-(methoxyphenyl)ethylamine in 5% overall yield (Scheme 6). In terms of sequential annulation, the strategy involves the following operations: E → DE → ABDE → ABCDE (Scheme 1). The key steps in the synthesis are the stereoselective formation of octahydroindol-6-ones by acid treatment of dihydroanisole derivatives, the regioselective Fischer indolization to obtain octahydropyrrolo[3,2-c]carbazoles, and the tandem process consisting of Pummerer rearrangement upon a β-amino sulfoxide and thionium ion cyclization upon a β-indole position of a 2,3-disubstituted indole to generate the quaternary spiro center. Attempts to effect the construction of the pentacyclic framework by means of Fischer indolization of the octahydropyrrolo[3,2,1-hi]indol-6-one resulted in failure (Scheme 2).
