21019-24-9

Upstream product

• 4880-92-6 apovincamine 
• 85588-92-7 (-)-methyl 1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine(1β-yl) pyruvate oxime 
• 186581-53-3 diazomethane 
• 59639-59-7 (10S,11aS,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carbonitrile 
• 59639-59-7 (10R,11aS,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carbonitrile 
• 59639-59-7 (+/-)-eburnane-16β-carbonitrile 
• 59656-84-7 (10R,11aR,11bR)-11a-Ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid amide 
• 106498-98-0 (1R*,5R*,12bR*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-methanol 
• 66685-08-3 1-ethyl-2,3,4,6,7,12-hexahydroindolo<2,3-a>quinolizin-4(1H)-one 
• 51152-47-7 (1R*,5S*,12bS*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-carbaldehyde 
• 66685-13-0 4-(4,9-dihydro-3H-β-carbolin-1-yl)-hexanoic acid methyl ester 
• 169530-52-3 (1R*,5R*,12bR*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-carbaldehyde 
• 74571-79-2 1-ethyl-2,3,4,6,7,12-hexahydroindolo<2,3-a>quinolizin-4-thione 
• 23944-42-5 (-)-1β-methoxycarbonylethyl-1α-ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine 

Downstream Products

• 23173-27-5 (13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-yl)-methanol 

Relevant academic research and scientific papers

Syntheses and Cardiovascular Activity of Stereoisomers and Derivatives of Eburnane Alkaloids

The synthesis of all the possible isomers of the eburnamenine-vincamine type alkaloids 1b, 2a*, 3a and derivatives 4, 8, 9, 10 is described.Structures were determined by 1H- and 13C-NMR spectroscopy including special techniques such as DR, DEPT, DNOE, and 2D-HSC.In contrast to the known cerebrovascular effects of cis-(3S,16S) compounds, trans-(3S,16R) derivatives show a significant peripheral vasodilator effect. Key Word: Eburnanes / Alkaloids / Cardiovascular effects / Indoloquinolizines

SYNTHESIS OF STEREOISOMERIC VINCAMINES

The synthesis of (+/-)-vincamine (I), (+/-)-16-epi-vincamine (XVIII) and (+/-)-16-epi-21-epivincamine (XVII) from 1-ethyl-2,3,4,6,7,12-hexahydroindoloquinolizine (IV) and 2-chloroacrylonitrile is described.It is characterized by a novel method of oxidation of the key intermediates, (+/-)-deoxyvincamine (II) and (+/-)-16-epi-21-epi-deoxyvincamine (XIII) with oxodiperoxymolybdenum (pyridine) (hexamethylphosphoric triamide).The deoxy derivatives II and XIII were prepared by direct or stepwise acid or alkaline hydrolysis od stereoisomeric (+/-)-eburnane-16-carbonitriles IX-XII, obtained by reduction of the primary immonium salt V, and subsequent esterification.In some cases, the hydrolysis is accompanied by epimerization at C(16).

A NEW APPROACH TO (+/-)-APOVINCAMINE

A new approach to (+/-)-apovincamine, 2, is reported which bypasses the formation of (+/-)-vincamine, 1, and includes the dehydration of the β-hydroxy ester 7, obtained by regio-controlled alkylation of the stereochemically suitable aldehyde 6 with methyl chloroacetate.Using ethyl chloroacetate, the clinically useful apovincamine analogue, (+/-)-Cavinton, 3, is obtained. (+/-)-Apovincamine is then converted to (+/-)-vincamine, 1, by base-catalyzed oxygenation of the mixture of (+/-)-dihydroapovincamines 8 and 9.