29347-15-7

Upstream product

• 2731-01-3 (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole 
• 1238046-59-7 C₇H₁₃NO₃ 
• 2555-05-7 3-methyl-2-pyrrolidinone 
• 104069-10-5 (+)-N¹-noreseroline O-methyl ether 
• 139115-75-6 2-iodo-4-methoxy-N-methylaniline 
• 29347-10-2 physostigmine 
• 104069-12-7 (3aR,8aS)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 153109-55-8 (R)-5-Methoxy-1,3-dimethyl-3-((E)-2-triisopropylsilanyloxy-vinyl)-1,3-dihydro-indol-2-one 
• 153109-56-9 (R)-3-(2-oxoethyl)-1,2-dihydro-5-methoxy-1,3-dimethyl-2-oxo[3H]indole 
• 153109-51-4 (Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid (2-iodo-4-methoxy-phenyl)-methyl-amide 
• 153109-50-3 (Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid 

Downstream Products

• 29347-10-2 physostigmine 
• 29347-11-3 (+)-physovenine 
• 136173-08-5 (3aR,8aR)-5-methoxy-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole 
• 136173-09-6 (+)-(3aR)-3a,8-dimethyl-2,3,3a,8a-tetrahydrofuro[2,3-b]indol-5-ol 
• 103957-95-5 (+)-physostigmine salicylate 
• 93185-42-3 O-(chloroethyl)eseroline 

Relevant academic research and scientific papers

Catalytic asymmetric synthesis of either enantiomer of the calabar alkaloids physostigmine and physovenine

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

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.

PRACTICAL SYNTHESIS OF UNNATURAL (+)-PHYSOSTIGMINE AND CARBAMATE ANALOGUES

Details of a synthesis of unnatural (+)-physostigmine (5) prepared from urea 1 via (+)-eseroline (4) are given.Preparation of (+)-octylcarbamate 6, (+)-benzylcarbamate 7, (+)-phenylcarbamate 8 and (+)-N-methylphysostigmine (9) from (+)-eseroline (4) is also described.

Comparison of (-)-Eseroline with (+)-Eseroline and Dihydroseco Analogues in Antinociceptive Assays: Confirmation of Rubreserine Structure by X-ray Analysis

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.

Synthesis of some quaternary ammonium alkylating agents and their effects on soman-inhibited acetylcholinesterase

A number of compounds were synthesized and tested for their ability to realkylate the phosphonate anion of 'aged', soman-inhibited acetylcholinesterase. None were found able to do so, but two of the compounds in particular, [2-(4-pyridyl)ethyl]diethylmethylammonium iodide and its 2-isomer, proved able to slow the rate of aging significantly.