219584-05-1

Basic information

• Product Name: C₂₇H₃₂N₂O₂
• Synonyms: C₂₇H₃₂N₂O₂
• CAS NO: 219584-05-1
• Molecular Weight: 416.563
• Mol File: 219584-05-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₂₇H₃₂N₂O₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₇H₃₂N₂O₂(219584-05-1)
• EPA Substance Registry System: C₂₇H₃₂N₂O₂(219584-05-1)

Safety Data

• Hazardous Substances Data: 219584-05-1(Hazardous Substances Data)

Upstream product

• 219583-98-9 (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde 
• 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 
• 217448-25-4 (6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole 
• 7348-71-2 (E)-1-bromo-2-pentene 
• 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 

Downstream Products

• 219584-09-5 C₂₇H₃₀N₂O 
• 219584-13-1 C₂₈H₃₂N₂O₂ 
• 219584-15-3 N_b-benzyl, N_b-21-secotalpinine 
• 219584-19-7 N_b-benzyltalcarpine 
• 38990-08-8 (-)-talcarpine 

Relevant articles and documents

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.