3247-10-7

Upstream product

• 55475-53-1 20-iodo-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester 
• 91208-71-8 C₂₁H₂₆N₂O₂ 
• 80658-39-5 C₂₁H₂₅ClN₂O₂ 
• 55856-70-7 19-Iodo-tabersonine 
• 77255-84-6 16-nitro-1,2-dehydro-2,16-dihydro vincadifformine 
• 74129-83-2 (-)-(hydroxymethyl)norvincadifformine 
• 32789-67-6 16-chloro-1-dehydro-vincadifformine 
• 80658-39-5 C₂₁H₂₅ClN₂O₂ 
• 74129-83-2 (+)-(hydroxymethyl)norvincadifformine 
• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 1451192-90-7 C₂₅H₂₈N₂O₃S 
• 1451192-94-1 C₂₃H₂₄N₂O₂S 
• 1451192-89-4 C₂₇H₃₂N₂O₃S₂ 
• 1451192-93-0 C₂₉H₃₆N₂O₃S₂ 

Downstream Products

• 55700-36-2 2,16-dihydrovincadifformine 
• 143207-13-0 (3aS,5S,5aS,10bS,12bS)-6-Acetyl-3a-ethyl-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester 
• 4880-92-6 apovincamine 
• 260362-01-4 14α-phenylselenenyl-3-oxo-(N_a-tert-butoxycarbonyl)-vincadifformine 
• 260362-12-7 14β-phenylselenenyl-3-oxo-(N_a-tert-butoxycarbonyl)-vincadifformine 
• 260362-00-3 14β-benzyl-3-oxo-(N_a-tert-butoxycarbonyl)vincadifformine 
• 260362-03-6 14β-benzyl-(N_a-tert-butoxy-carbonyl)vicadifformine 
• 260362-08-1 14β-benzyl-1,2-didehydroaspidospermidine 
• 19751-76-9 (+)-1,2-didehydroaspidospermidine 
• 18374-17-9 (±)-vincadifformine 
• 1617-90-9 vincamin 
• 1617-90-9 14-hydroxy-14,15-dihydro-eburnamenine-14-carboxylic acid methyl ester 
• 56245-51-3 (-)-dehydro-1,2 aspidospermidine 
• 38199-30-3 Δ¹⁴-vincamenine 

Relevant academic research and scientific papers

Rearrangement and photolysis of aziridines in the aspidosperma series

Rearrangement of aziridine 1 by MgBr2 gave 2-H-dihydro-17- dehydrovincadifformine 6. Photolysis transformed aziridines 1 and 11 into the new compounds 1,2-seco-1,21-cyclovincadifformine 10 and 1,2-seco-1,21- cyclotabersonine 12.

Preparation method of high-purity vinpocetine (by machine translation)

The preparation method, of the high-purity vinpocetine :S1. comprises, following steps: preparing vinpocstine, by dissolving; in toluene as a solvent; in toluene as a solvent ;S2. and carrying out an ester exchange reaction, to obtain the intermediate vinpocstine nitrogen oxide, in a toluene as a solvent, and carrying out an ester exchange reaction to obtain a product impurity at least ;S3. purity S2 and, % by mass of a solvent . The preparation method of the vinpocstine nitrogen oxide reaction solution in step, is adopted as a catalyst for carrying out an ester exchange reaction to obtain a long spring cavoniflorac sodium/vinpocstine . The process production operation is, simple, avoids the high, 99.9% toxicity reagent, to obtain a, long spring cavonift, nitrogen oxide reaction, solution to, obtain a product, impurity at a time of acid. (by machine translation)

Asymmetric Total Synthesis of Vincadifformine Enabled by a Thiourea-Phosphonium Salt Catalyzed Mannich-Type Reaction

An asymmetric total synthesis of vincadifformine is described. The limited tactics with chiral cation-directed catalysis in total synthesis inspired the development of our strategy for accessing this alkaloid in enantionrich form. The route features a thiourea–phosphonium salt catalyzed Mannich-type reaction, a phosphine-promoted aza-Morita–Baylis–Hillman reaction and a trifluoroacetic acid promoted deprotection/amidation cascade process.

Biosynthesis of an Anti-Addiction Agent from the Iboga Plant

(-)-Ibogaine and (-)-voacangine are plant derived psychoactives that show promise as treatments for opioid addiction. However, these compounds are produced by hard to source plants, making these chemicals difficult for broad-scale use. Here we report the complete biosynthesis of (-)-voacangine, and de-esterified voacangine, which is converted to (-)-ibogaine by heating, enabling biocatalytic production of these compounds. Notably, (-)-ibogaine and (-)-voacangine are of the opposite enantiomeric configuration compared to the other major alkaloids found in this natural product class. Therefore, this discovery provides insight into enantioselective enzymatic formal Diels-Alder reactions.

Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (-)-Aspidospermidine, (-)-Tabersonine, and (-)-Vincadifformine

The development and application of the arene-fused domino Michael/Mannich route to the tetrahydrocarbazole (ABE) core of Aspidosperma alkaloids is described. The scope of this novel transformation was studied in terms of the nucleophilic component (i.e., N-sulfinyl metallodienamine) and the electrophilic component (i.e., Michael acceptor). The successful application of this methodology toward the concise total syntheses of classical indole alkaloids (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine in 10-11 steps, respectively, is also discussed.

Vincamine preparation method

The invention relates to a vincamine preparation method in the field of compound preparation. The vincamine preparation method includes the steps of (1), tabersonine preparation, (2), vincadifformine preparation, (3), monoperoxy maleic acid preparation and (4), vincamine preparation. The vincamine preparation method has the advantages of easy availability to raw materials, simplicity and convenience in reaction process operation, high safety, low cost, high product yield, high quality and suitability for industrial production.

Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (-)-Quebrachamine, (+)-Aspidospermidine, (-)-Aspidospermine, (-)-Pyrifolidine, and Related Natural Products

A uniformly strategic total synthesis of Aspidosperma alkaloids (+)-vincadifformine, (-)-quebrachamine, (+)-aspidospermidine, (-)-aspidospermine, (-)-pyrifolidine, and nine others from efficiently constructed tricyclic ketone 13 is reported. Highlights of these divergent and practical syntheses include (i) stereoselective intermolecular [4 + 2] cycloaddition to establish a C-E ring with one all-carbon quaternary stereocenter (C-5) and two bridged contiguous cis-stereocenters (C-12 and C-19), (ii) a Pd/C-catalyzed hydrogenation/deprotection/amidation cascade process to assemble the D ring, and (iii) Fischer indolization to forge the A-B ring.

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of "classic" natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.

Domino Michael/Mannich/ N-alkylation route to the tetrahydrocarbazole framework of Aspidosperma alkaloids: Concise total syntheses of (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine

We report a novel, asymmetric domino Michael/Mannich/N-alkylation sequence for the rapid assembly of the tetrahydrocarbazole framework of Aspidosperma alkaloids. This method was utilized in the concise total syntheses of classical targets (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine in 10 or 11 steps. Additional key steps include ring-closing metathesis to prepare the D-ring and Bosch-Rubiralta spirocyclization to prepare the C-ring.

Collective synthesis of natural products by means of organocascade catalysis

Organic chemists are now able to synthesize small quantities of almost any known natural product, given sufficient time, resources and effort. However, translation of the academic successes in total synthesis to the large-scale construction of complex natural products and the development of large collections of biologically relevant molecules present significant challenges to synthetic chemists. Here we show that the application of two nature-inspired techniques, namely organocascade catalysis and collective natural product synthesis, can facilitate the preparation of useful quantities of a range of structurally diverse natural products from a common molecular scaffold. The power of this concept has been demonstrated through the expedient, asymmetric total syntheses of six well-known alkaloid natural products: strychnine, aspidospermidine, vincadifformine, akuammicine, kopsanone and kopsinine.