217448-25-4

Upstream product

• 7348-71-2 (E)-1-bromo-2-pentene 
• 217448-24-3 (6S,10S)-(-)-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole 
• 100-52-7 benzaldehyde 
• 913556-71-5 C₂₈H₂₆N₂O₂S 
• 4299-70-1 D-Tryptophan methyl ester 
• 197143-14-9 (6S,10S)-(-)-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate 
• 197143-13-8 (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole 
• 84094-75-7 cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 84094-74-6 (1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 63229-68-5 D-(+)-N_bbenzyltryptophan methyl ester 

Downstream Products

• 217448-26-5 (6S,10S)-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde 
• 143065-03-6 (6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-oxomethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]-indole 
• 328529-34-6 (6S,9S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]-indolyl-9-acetal 
• 328529-33-5 C₂₉H₃₄N₂O₂ 
• 217448-31-2 (6S,13S)-4-ethyl-6,7,12,13-tetrahydro-14-(phenylmethyl)-6,13-imino-5H-pyrido[3',4':5,6]cyclooct[1,2-b]indole 
• 217448-27-6 (6S,10S)-8-(1'-ethyl-2'-propenyl)-9-(2',5'-dioxacyclopentanyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole 
• 217448-28-7 (6S,10S)-8-(1'-ethyl-2'-acetyl)-9-(2',5'-dioxacyclopentanyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole 
• 217448-29-8 C₂₆H₂₈N₂O₂ 
• 245760-13-8 C₂₉H₃₆N₂O₄ 
• 245760-13-8 C₂₉H₃₆N₂O₄ 
• 219584-13-1 C₂₈H₃₂N₂O₂ 
• 219584-05-1 C₂₇H₃₂N₂O₂ 
• 219584-02-8 (6S,10S)-5-methyl-8-(pent-2'-enyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indolyl-9-hydroxymethane 
• 219584-09-5 C₂₇H₃₀N₂O 

Relevant academic research and scientific papers

Enantiospecific total synthesis of (-)-(E)16-epiaffinisine, (+)-(E)16-epinormacusine B, and (+)-dehydro-16-epiaffinisine as well as the stereocontrolled total synthesis of alkaloid G

An efficient strategy is described for the total synthesis of the sarpagine-related indole alkaloids (-)-(E)16-epiaffinisine (1), (+)-(E)16-epinormacusine B (2), and (+)-dehydro-16-epiaffinisine (4). A key step employed the chemospecific and regiospecific

Stereocontrolled Total Synthesis of Alkaloid G via the Oxy-anion Cope Rearrangement and Improved Total Synthesis of (+)-Ajmaline

(Matrix Presented) The oxy-anion Cope rearrangement followed by protonation of the enolate which resulted under conditions of kinetic control has been employed to generate the key asymmetric centers at C(15), C(16), and C(20) in alkaloid G (1) and (+)-ajm

Enantiospecific Total Synthesis of the Sarpagine Related Indole Alkaloids Talpinine and Talcarpine as Well as the Improved Total Synthesis of Alstonerine and Anhydromacrosalhine-methine via the Asymmetric Pictet-Spengler Reaction

The enantiospecific total synthesis of talpinine 1 and talcarpine 2 has been accomplished from D-(+)-tryptophan in 13 steps (11 reaction vessels) in 10% and 9.5% overall yields, respectively. Moreover, this synthetic approach has been employed for the improved synthesis of alstonerine 3 and anhydromacrosalhine-methine 4 in 12% and 14% overall yield, respectively. A convenient synthetic route for the enantiospecific, stereospecific preparation of the key intermediate (-)-Na-H, Nb-benzyl tetracyclic ketone 15a via the asymmetric Pictet-Spengler reaction on a multihundredgram scale has been developed. A diastereocontrolled (>30:1) anionic oxy-Cope rearrangement and the intramolecular rearrangement to form ring-E and an Nb-benzyl/Nb-methyl transfer reaction also served as key steps. This general approach can now be utilized for the synthesis of macroline/ sarpagine related indole alkaloids and their antipodes for biological screening.

General approach for the synthesis of ajmaline/sarpagine indole alkaloids: Enantiospecific total synthesis of (+)-ajmaline, alkaloid G, and norsuaveoline via the asymmetric Pictet-Spengler reaction

A general approach (oxyanion-Cope strategy) for the synthesis of sarpagine/ajmaline indole alkaloids has been developed. (+)-Ajmaline 1 and alkaloid G 2 as well as norsuaveoline 3 have been synthesized from D-(+)-tryptophan in enantiospecific fashion via

The enantiospecific total synthesis of norsuaveoline

Norsuaveoline la has been synthesized enantiospecifically in 28% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled oxy-anion Cope rearrangement as key steps.