473-99-4

Usage

InChI:InChI=1/C19H24N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,16,18,22H,2,5,8-12H2,1H3/t16-,18-,19+/m0/s1

Upstream product

• 111687-23-1 19-oxoeburnamonine 
• 4880-88-0 vinburnine 
• 111687-22-0 (1S,12bS)-1-ethyl-1-(2-hydroxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine 
• 111687-25-3 (1S,12bR)-1-ethyl-1-(2-hydroxyethyl)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine 
• 102631-76-5 3-Ethyl-3-((E)-2-nitro-vinyl)-tetrahydro-pyran-2-one 
• 111154-23-5 3-(3-Ethyl-2-methoxy-tetrahydro-furan-3-yl)-propionic acid 
• 111154-20-2 3-Ethyl-5-hydroxy-3-(3-hydroxy-propyl)-dihydro-furan-2-one 
• 199190-53-9 3-(3-Ethyl-2-oxo-tetrahydro-furan-3-yl)-propionic acid 
• 1354568-46-9 (S)-2-allyl-2-ethyl-N-benzoyl-δ-valerolactam 

Downstream Products

• 1617-90-9 vincamin 
• 2580-88-3 (-)-eburnamonine 
• 4880-88-0 vinburnine 
• 65026-49-5 (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^2,7.0^8,18.0^15,19]nonadeca-2,4,6,8⁽¹⁸⁾-tetraene 

Relevant academic research and scientific papers

Intermediate and preparation method and application thereof in synthesis of vinorchine

The invention relates to the technical field of chemical drug synthesis, and discloses an application of an intermediate or a preparation method thereof in synthesis of vinorchin, adopts a modular synthetic strategy, adopts the compound D with 1 ring structures and C20 quaternary carbon centers, 5 (i.e. the compound 5) as a synthesis building block. The operation is simple and reaction conditions are easy for large-scale amplification effect.

Intermediate, preparation method and application of intermediate in synthesis of vincamine

The invention relates to the technical field of chemical drug synthesis, and discloses an intermediate, a preparation method and application of the intermediate in synthesis of vincamine. A modular synthesis strategy is adopted, and a compound 1 with a D ring structure and a C20 quaternary carbon center and a tryptophol derivative 7 (namely the compound 7) with an indole ring are adopted as synthesis blocks for synthesis. The synthesis method is efficient; each step of the synthesis route is simple in reaction; the used reagent and solvent are cheap and easy to obtain; the operation is simple and convenient; the yield is high; and large-scale production is easy.

Synthesis of eburnamine, isoeburnamine, and eburnamonine via a spirocyclic intermediate

Racemic eburnamonine (1) was synthesized via 6, an intermediate possessing local symmetry. Cleavage of the cyclopentene subunit led to pentacyclic aldehydes 8a/8b which on subsequent borohydride and Wolff-Kishner reductions gave 12. The final steps included a RuCl3-catalyzed periodate oxidation and pyridinium chlorochromate (PCC) oxidation. The penultimate intermediates were racemic eburnamine (2) and racemic isoeburnamine (3).

Synthesis of Vinca Alkaloids and Related Compounds. Part LXVIII. Two Diastereoisomeric Aspidosperma-Eburnea Type Bis-indoles: Their Synthesis and Structure Revisited

With the aim of clarifying their previously incorrectly depicted structure, the indole-indoline type compounds 11 and 12 were synthesized via different routes.The results presented here are a detailed account of the synthetic aspects of this work, and also redress some points of an earlier paper on this topic.

STRUCTURE OF GONIOMITINE, A NEW TYPE OF INDOLE ALKALOID

The structure 1 proposed for goniomitine, an indole alkaloid isolated from the root bark of Gonioma malagasy (Apocynaceae), was inferred from an analysis of its MS, 1H and 13C NMR spectral data.A biogenetic scheme is proposed to account for the formation of 1 from vincadifformine 9.

METHODS FOR INDOLE ALKALOID SYNTHESIS: REACTIONS OF N-ARYLSULFONYLENAMINES WITH ELECTROPHILES. AN EXPEDITIOUS SYNTHESIS OF (+/-)-EBURNAMONINE.

Treatment of 4 with MCPBA gave 9.The pentacyclic amide 3 on exposure to cyanogen chloride gave the cis-chloro-hydrin 20, and the geminal dichloride 21.When 21 was treated with HCl/MeOH it rapidly rearranged to eburnamonine lactam 22.

Total Synthesis of (-)-Kopsinilam, (-)-Kopsinine, and the Bis-indole Alkaloids (-)-Norpleiomutine and (-)-Pleiomutine

The racemic tetracyclic amine (5) was resolved and converted into (-)-kopsinine (16); subsequent coupling to (-)-eburnamine (2) gave (-)-norpleiomutine (4).

Synthetic Approach to (+/-)- Vincamine via Cleavage of an α-Diketone Monothioacetal. Alternative Synthesis of (+/-)-Eburnamine, (+/-)-Isoeburnamine, and (+/-)-Eburnamenine

The half ester (8) prepared from cleavage of 2-(1,3-dithian-2-yl)-4-ethoxycarbonyl-4-ethylcyclohexanone (7) has been converted into (+/-)-eburnamine (20), (+/-)-isoeburnamine (21), and (+/-)-eburnamenine (22) by a stereospecific reaction sequence proceeding via the dithian intermediate (16).However an attempted conversion of (16) into (+/-)-vincamine (6) was unsuccessful.