66859-30-1Relevant academic research and scientific papers
Synthesis of vinca alkaloids and related compounds. Part 101: A new convergent synthetic pathway to build up the aspidospermane skeleton. Simple synthesis of 3-oxovincadifformine and 3-oxominovincine. Attempts to produce 15β-hydroxyvincadifformine
éles, János,Kalaus, Gy?rgy,Greiner, István,Kajtár-Peredy, Mária,Szabó, Pál,Szabó, Lajos,Szántay, Csaba
, p. 8921 - 8927 (2007/10/03)
A molecule with an indole skeleton, containing a latent acrylic ester function - acting as a diene - was produced from Nb-trityl-2-(hydroxy-methyl)-tryptamine and reacted with esters containing an aldehyde or aldehyde-equivalent structural unit, yielding 3-oxo-16,17-dihydro-Δ20-secodin-17-ol type intermediates from which dehydration, followed by [4+2]cycloaddition, furnished 3-oxovincadifformine and 3-oxominovincine. We also wished to apply the method to produce 15β-hydroxyvincadifformine, however, the appearance of a dimeric product with indole skeleton was observed instead of the expected cycloaddition.
Synthesis of vinca alkaloids and related compounds, Part LXXXIX. Some unexpected reactions of compounds containing the D-seco-aspidospermane ring system
Kalaus, Gyoergy,Juhasz, Imre,Steinhauser, Kinga,Greiner, Istvan,Kajtar-Peredy, Maria,Brlik, Janos,Szabo, Lajos,Szantay, Csaba
, p. 205 - 219 (2007/10/03)
Interaction of the tryptamine derivative (3) with the formyl ester (4) gave (±)-20-deethyl-2,16-didehydro-14,16-bis(methoxycarbonyl)-3-phenyl-3,14- seco-20-epiaspidospermidine (7) instead of the expected acetal (6). The product of the reaction of 3 with t
Synthesis of Vinca Alkaloids and Related Compounds. 63. A New Synthetic Pathway for Preparing Alkaloids and Related Compounds with the Aspidosperma Skeleton. Total Syntheses of (+/-)-Vincadifformine, (+/-)-Tabersonine, and (+/-)-3-Oxotabersonine
Kalaus, Gyoergy,Greiner, Istvan,Kajtar-Peredy, Maria,Brlik, Janos,Szabo, Lajos,Szantay, Csaba
, p. 1434 - 1442 (2007/10/02)
Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of (2-ethoxycarbonyl)tryptamine (2).The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43).The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tricyclic benzoate esters 37 and 38.The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.
Biomimetic Syntheses of Indole Alkaloids. 11. Syntheses of β-Carboline and Indoloazepine Intermediates
Kuehne, M. E.,Bohnert, J. C.,Bornmann, W. G.,Kirkemo, C. L.,Kuehne, S. E.,et al.
, p. 919 - 924 (2007/10/02)
The preparation and rearrangement of α-carbomethoxy-α-(chloromethyl)tetrahydro-β-carbolines (9a,b) provided methyl 1,2,3,6-tetrahydroazepinoindole-5-carboxylates (10a,b) and derivatives, which serve as intermediates in a series of alkaloid synthese
Studies in Biomimetic Alkaloid Syntheses. 5. Total Syntheses of ψ-Vincadifformine, 20-Epi-ψ-vincadifformine, Pandoline, 20-Epipandoline and the C-16 Epimeric (Carbomethoxy)velbanamines.
Kuehne, Martin E.,Kirkemo, Curtis L.,Matsko, Thomas H.,Bohnert, John C.
, p. 3259 - 3265 (2007/10/02)
The title racemic pentacyclic alkaloids (5b-e) were synthesized by respective reactions of the indoloazepines 8b,c with the halopentanals 10a,b or the epoxypentanal 23.Reductive opening of pandoline (5d) gave the racemic seco compounds 28a,b, and reductiv
Preparation of vincadifformine
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, (2008/06/13)
The invention relates to the preparation of vincadifformine. Tetrahydro-β-carboline (II) is reacted with benzoyl chloride to provide 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-[3,4b]-indole (III). Then compound (III) is reduced to give 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4b]-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into chloroindolenine derivative (V) which is immediately treated with thallium t-butyl methyl malonate to give t-butyl methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (VII). Compound (VII) is hydrogenated to give methyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (IX). In an alternative embodiment, compound (VI) can be hydrogenated to methyl t-butyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VIII) which is then decarboxylated into compound (IX). Compound (IX) is condensed with 1-bromo-4-formyl-hexane to yield vincadifformine (I).
