466-85-3

Usage

InChI:InChI=1/C19H22N2O2/c22-18-16-12-9-15-19(6-7-21(15)10-11(12)5-8-23-18)13-3-1-2-4-14(13)20-17(16)19/h1-5,12,15-18,20,22H,6-10H2/t12-,15-,16+,17-,18+,19+/m0/s1

Upstream product

• 24180-60-7 (17R,19E)-1-cyanoformyl-17,18-epoxy-cur-19-en-17-ol; hydrochloride 
• 24180-59-4 23-isonitrosostrychnine 
• 609-73-4 o-nitroiodobenzene 
• 504-02-9 1,3-cylohexanedione 
• 138040-05-8 3-hydroxy-2-(2-nitrophenyl)cyclohex-2-enone 
• 138040-06-9 3-allyloxy-2-(o-nitrophenyl)-2-cyclohexenone 
• 138040-07-0 2-Allyl-2-(2-nitrophenyl)-1,3-cyclohexanedione 
• 152425-13-3 (4R)-1-(trimethylstannyl)-4-<1-((triisopropylsiloxy)methyl)-3-tert-butoxy-1(E)-propenyl>cyclopentene 
• 130749-97-2 1,3-dimethyl-5-(2-iodophenyl)-hexahydro-2-oxo-1,3,5-triazine 
• 219650-31-4 (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(methoxycarbonyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates 
• 112791-25-0 methyl (3aS,5R,6S,6aS,11bS,E)-12-(2-hydroxyethylidene)-1,2,3a,4,5,6,6a,7-octahydro-3,5-ethanopyrrolo[2,3-d]carbazole-6-carboxylate 
• 152425-19-9 (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E)-<(hydroxymethyl)methylene>-1H-pyrrolo<2,3-d>carbazole-6-carboxylates 
• 222162-01-8 (3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one 
• 222162-02-9 (1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.0^4,8]undecan-11-one 

Downstream Products

• 2864-87-1 (17R,19E)-17-acetoxy-1-acetyl-17,18-epoxy-cur-19-ene 
• 2871-28-5 henningsamine, O-acetyldiaboline A 
• 57-24-9 strychnidin-10-one 
• 109356-00-5 C₂₅H₂₆N₂O₂S 
• 509-40-0 diaboline 

Relevant academic research and scientific papers

Probing the pharmacophore for allosteric ligands of muscarinic M 2 receptors: SAR and QSAR studies in a series of bisquaternary salts of caracurine V and related ring systems

Allosteric effects on muscarinic acetylcholine M2 receptors were examined in a series of bisquaternary salts of the Strychnos alkaloid caracurine V (6) and related iso-caracurine V, tetrahydrocaracurine V, and bisnortoxiferine ring systems. The

Enantioselective Total Synthesis of Wieland-Gumlich Aldehyde and (-)-Strychnine

A total synthesis of (-)-strychnine in 15 steps from 1,3-cyclohexanedione in 0.15% overall yield is described. The sequence followed in the assembling of rings is: E → AE [2-(2-nitrophenyl)-1,3-cyclohexanedione] → ACE (3a-aryloctahydroindol-4-one) → ACDE (arylazatricyclic core) → ABCDE (strychnan skeleton) → ABCDEF (Wieland-Gumlich aldehyde) → ABCDEFG (strychnine). The key steps of the synthesis are the enantioselective construction of the 3a-(2-nitrophenyl)-octahydroindol-4-one ring system and the closure of the piperidine ring by a reductive Heck cyclization to generate the pivotal intermediate (-)-14. In contrast, a Lewis acid promoted α-alkoxy-propargylic silane-enone cyclization did not lead to synthetically useful azatricyclic ACDE intermediates. The introduction of C-17 and the closure of the indoline ring by reductive amination of the α-(2-nitrophenyl) ketone moiety complete the strychnan skeleton from which, via the Wieland-Gumlich aldehyde, the synthesis of (-)-strychnine is achieved.

Total synthesis of (-)-strychnine via the Wieland - Gumlich aldehyde

Fifteen steps suffice for an enantioselective total synthesis of (-)- strychnine (1) from 1,3-cyclohexanedione. The key steps are the easy generation of the enantiopure intermediate 2, the closure of the piperidine ring by a reductive Heck reaction, and the elaboration of the indoline nucleus in an advanced synthetic stage. TBDMS = tert-butyldimethylsilyl.

Syntheses of strychnan- and aspidospermatan-type alkaloids. 10. An enantioselective synthesis of (-)-strychnine through the Wieland-Gumlich aldehyde

Condensations of L-tryptophan-derived 2-[(methoxycarbonyl)methyl]-3- [2(S)-(benzyloxycarbonyl)-2-(N(b)-benzylamino)ethyl]indole (6) with 4,4- dimethoxyacrolein or with 2,4-hexadienal, followed by removal of the tryptophanyl ester function, respectively gave the tetracyclic acetal (-)- methyl (2S,-3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5- (dimethoxymethyl)-1H-pyrrolol[2,3-d]carbazole-6-carboxylate (10) or the tetracyclic olefin (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7- hexahydro-5-(1-propenyl)-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (14). Their respective hydrolysis or oxidation provided, enantioselectively, the tetracyclic aldehyde (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7- hexahydro-5-formyl-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (5). Its reaction with tri-n-butyl-1-(ethoxy)ethoxymethyltin and n-butyllithium, followed by oxidation of the resultant alcohol (-)-methyl (2S,3aS,5R,11bR)-3-benzyl- 2,3,3a,4,5,7-hexahydro-5-(1ξ-hydroxy-2-((1-ethoxy-ethoxy))ethyl-1H- pyrrolo[2,3-d]carbazole-6-carboxylate (16) and cyclization furnished the pentacyclic ketone (-)-methyl (2S,3aS,SR,11bR)-3-benzyl-2,3,3a,4,5,7- hexahydro-3,5-ethano-12-oxo-1H-pyrrolo-[2,3-d]carbazole-6-carboxylate (15). A Horner-Emmons condensation led to the unsaturated esters (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-(E and Z)- [(methoxycarbonyl)-methylene]-1H-pyrrolo[2,3-d]carbazole-6-carboxylates (19 and 20) with 17:1 E/Z selectivity. Reductions of the ester and vinylegous urethane functions in 19 led to the Wieland-Gumlich aldehyde 3 as a 6:1 anomeric hemiacetal mixture. Its condensation with malonic acid provided (- )-strychnine (1) in 5.3% overall yield and 14 steps from the tryptophan derivative 6.

Synthesis and Hypotensive Activity of Diaboline

Diaboline (4) has been prepared from strychnine through 23-isonitrosostrychnine (1) and Wieland-Gumlich aldehyde (2).It exhibits a significant hypotensive activity in anaesthetized rats and the effect is dose related.The fall in blood pressure appears to be due to the depressant effect on myocardium.