29347-15-7Relevant articles and documents
Catalytic asymmetric synthesis of either enantiomer of the calabar alkaloids physostigmine and physovenine
Matsuura, Takaharu,Overman, Larry E.,Poon, Daniel J.
, p. 6500 - 6503 (1998)
A potentially versatile asymmetric route to hexahydropyrrolo[2,3-b]indoles having carbon substituents at C-3a (Scheme 1) is demonstrated through enantioselective total syntheses of the Calabar alkaloids (-)physostigmine (2), (-)-physovenine (10), and their enantiomers. The synthesis of enantiopure (-)physostigmine proceeds from commercially available 2-butyn-1-ol (11) and N-methyl-p-anisidine (15) in 15-20% overall yield by way of eight isolated and purified intermediates. The central step is catalytic asymmetric Heck cyclization of (Z)-2-methyl-2-butenanilide 17 to-form oxindole aldehyde (S)-19 in 84% yield and 95% ee.
Synthesis of (+)-phenserine using an interrupted Fischer indolization reaction
Schammel, Alex W.,Chiou, Grace,Garg, Neil K.
supporting information; experimental part, p. 725 - 728 (2012/03/26)
A concise synthesis of the Alzheimer's therapeutic (+)-phenserine is described. The approach features an interrupted Fischer indolization to construct the pyrrolidinoindoline core, in addition to a classical resolution to arrive at phenserine in enantioenriched form.
Comparison of (-)-Eseroline with (+)-Eseroline and Dihydroseco Analogues in Antinociceptive Assays: Confirmation of Rubreserine Structure by X-ray Analysis
Schoenenberger, Bernhard,Jacobson, Arthur E.,Brossi, Arnold,Streaty, Richard,Klee, Werner A.,et al.
, p. 2268 - 2273 (2007/10/02)
The enantiomers of eseroline bind to opiate receptors of rat brain membranes with equal affinities and show opiate agonist properties as inhibitors of adenylate cyclase in vitro.However, only (-)-eseroline shows potent narcotic agonist activity in vivo, similar to that of morphine.Neither (-)-noreseroline, (+)-eseroline, nor the open dihydroseco analogue (-)-8 shows analgetic effects in vivo.The structure of rubreserine being a resonance hybrid of an o-quinone with its zwitterionic mesomer is confirmed by solid-state X-ray diffraction analysis.