85622-00-0

Upstream product

• 79-37-8 oxalyl dichloride 
• 1575-73-1 2-ethyl-pent-4-enoic acid 
• 42998-02-7 methyl 2-ethyl-4-pentenoate 

Downstream Products

• 18374-17-9 (±)-vincadifformine 
• 121074-25-7 (4R,5S)-3-((R)-2-Ethyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 121074-25-7 (4R,5S)-3-[(2S)-1-oxo-2-ethyl-4-pentenyl]-4-methyl-5-phenyl-2-oxazolidinone 
• 121074-31-5 N^b-benzyl-21-<(tert-butyldimethylsilyl)oxy>-D-seco-Ψ-vincadifformine 
• 121074-31-5 N^b-benzyl-21-<(tert-butyldimethylsilyl)oxy>-D-seco-Ψ-vincadifformine 
• 109704-79-2 (S)-3-Benzyl-4-((R)-2-hydroxymethyl-butyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester 
• 109704-79-2 (S)-3-Benzyl-4-((S)-2-hydroxymethyl-butyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Syntheses of 20'-Deoxyvinblastine, 20'-Deoxyleurosidine, 20'-Deoxyvincovaline, 20'-epi-20'-Deoxyvincovaline, and 20'-Deoxyvincristine and Its 20'-Epimer through Racemic and Enantioselectively Generated Intermediates. New Syntheses of D/E-cis- and -trans-Ψ

Vindoline (20), on reaction with chloro imine derivatives of the D-seco-D/E-trans-Ψ- and -20-epi-Ψ-vincadifformines 18 and 19, followed by cyclization and debenzylation steps, provided the natural products 20'-deoxyvinblastine (4) and 20'-deoxyleurosidine

Studies in Biomimetic Alkaloid Syntheses. 8. Total Syntheses of the C-14 Epimeric Hydroxyvincadifformines, Tabersonine, a (Hydroxymethyl)-D-norvincadifformine, and the C-20 Epimeric Pandolines

Condensation of methyl 1,2,3,4,5,6-hexahydroazepinoindole-5-carboxylate (6) with 5-chloro-2-ethyl-4-hydroxypentanal lactol (14) yielded the 14α- and 14β-hydroxyvincadifformines (8a,b) in an epimeric ratio which was solvent dependent.On condensation of the indoloazepine 6 with 4,5-epoxy-2-ethylpentanal (9) the same compounds were formed together wih a (hydroxymethyl)-D-norvincadifformine, 10, as the major product.Dehydration of 14β-hydroxyvincadifformine (8a) readily gave tabersonine (1), while 14α-hydroxyvincadifformine (8b) could only be dehydrated bycarbamate pyrolysis.The latter compound (8b) and the (hydroxymethyl)-D-norvincadifformine 10 could be converted to vincadifformine (18) through the chloromethyl derivative 16.Condensation of the indoloazepine 6 with the epimeric 4,5-dichloro-2-ethylpentanals (19) also gave the (chloromethyl)-D-norvincadifformine 16 and 14β-chlorvinacadifformine (20).Dehydrohalogenation of the latter compound provided a third sequence to tabersonine (1).A synthesis of the C-20 epimeric pandolines (2a,b) from 5-chloro-4-ethyl-4-hydroxypentanal lactol (22) similarly allowed control of the C-20 epimeric product ratio through its solvent dependence.