77080-67-2

Upstream product

• 100-39-0 benzyl bromide 
• 77080-61-6 C₁₈H₂₂N₂O₂ 
• 66859-22-1 methyl 1,2,3,4,5,6-hexahydroazepino<4,5-b>indole-5-carboxylate 
• 123-72-8 butyraldehyde 
• 146681-75-6 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester 
• 922-63-4 ethylacrolein 
• 153000-65-8 2-<(methoxycarbonyl)methyl>-3-<2-(N^b-benzylamino)ethyl>indole 
• 66859-30-1 methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate 

Downstream Products

• 132751-10-1 trans-N^b-benzyl-16-(methoxycarbonyl)-14-ethyl-D-norcleavamine 
• 132751-10-1 cis-N^b-benzyl-16-(methoxycarbonyl)-14-ethyl-D-norcleavamine 

Relevant 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

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 94 [1]. Epimerization of compounds with aspidospermane and D-secoaspidospermane skeleton [section]

The individual epimerization steps of vincadifformine (1), deethylvincadifformine isomers (2,3), their synthetic intermediates (4-13) as well as that of simpler compounds with D-secoaspidospermane skeleton (1517) were studied a) in protic medium (boiling deuteroacetic acidic) and b) under reductive (with sodium borodeuteride in boiling acetic acid, or with sodium borohydride in boiling deuteroacetic acid) conditions.

Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 9.1 The Enantioselective Generation of Tetracyclic ABCE Intermediates by a Tandem Condensation, [3,3]-Sigmatropic Rearrangement, and Cyclization Sequence

Reactions of substituted acroleins with the tryptophan-derived benzyl 2-(benzylamino)-3-[3-[2-[(methoxycarbonyl)methyl]indolyl]]propionate gave tetracyclic hexahydro-1H-pyrrolo[2,3-d] intermediates with stereoselective placement of substituents for cycliz