38990-08-8

Basic information

• Product Name: (20β)-20,21-Dihydro-21-methyl-18-noralstphyllan-19-al
• Synonyms: (20β)-20,21-Dihydro-21-methyl-18-noralstphyllan-19-al;Talcarpine
• CAS NO: 38990-08-8
• Molecular Formula: C21H26N2O2
• Molecular Weight: 338.44334
• Mol File: 38990-08-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (20β)-20,21-Dihydro-21-methyl-18-noralstphyllan-19-al(CAS DataBase Reference)
• NIST Chemistry Reference: (20β)-20,21-Dihydro-21-methyl-18-noralstphyllan-19-al(38990-08-8)
• EPA Substance Registry System: (20β)-20,21-Dihydro-21-methyl-18-noralstphyllan-19-al(38990-08-8)

Safety Data

• Hazardous Substances Data: 38990-08-8(Hazardous Substances Data)

Usage

Description

A carboline alkaloid, this base is a constituent of the stem bark of Pleiocarpa talbotii Wernham and forms colourless crystals from a mixture of Me2CO, Et20 and n-hexane. The structure has been established from spectroscopic data.

References

Naranjo et a!., Helv. Chim. Acta, 55, 752 (1972)

Upstream product

• 219584-19-7 N_b-benzyltalcarpine 
• 38989-99-0 (19S)-17,19-epoxy-1-methyl-(20αH)-19,20-dihydro-sarpagan-21α-ol 
• 74-88-4 methyl iodide 
• 133761-68-9 Carbonic acid benzyl ester (3S,4R,12bS,13S)-3-ethyl-13-formyl-12-methyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-4-yl ester 
• 133761-68-9 Carbonic acid benzyl ester (3S,4R,12bS,13R)-3-ethyl-13-formyl-12-methyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-4-yl ester 
• 509-37-5 ajmaline 
• 133761-67-8 Carbonic acid benzyl ester (3S,4R,8S,13aR)-3-ethyl-8-hydroxy-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indol-4-yl ester 
• 133761-69-0 Carbonic acid benzyl ester (3S,4R,12bS)-3-ethyl-13-hydroxymethyl-12-methyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-4-yl ester 
• 133761-71-4 C₂₈H₃₄N₂O₂Se 
• 133761-70-3 C₂₁H₂₈N₂O₂ 
• 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 
• 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 

Downstream Products

• 16101-12-5 macrocarpine B 
• 16101-12-5 macrocarpine A 

Relevant articles and documents

Total Synthesis of Sarpagine-Related Bioactive Indole Alkaloids

Extension of the asymmetric Pictet–Spengler reaction to bulkier Nb-alkylated tryptophan derivatives resulted in an improved stereospecific access to the key bicyclo[3.3.1]nonane core of bioactive C-19 methyl substituted sarpagine/macroline/ajmaline indole alkaloids with excellent diastereoselectivity by internal asymmetric induction. Complete stereocontrol of the C-19 methyl function in either the α- or β-configuration was achieved, which enables the total synthesis of any member from this group of thirty alkaloids. We report herein, the total synthesis of macrocarpines (A-C) 1–3, talcarpine 4, N(4)-methyl-N(4),21-secotalpinine 5, dihydroperaksine 8 and deoxyperaksine 9.

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.

An efficient synthetic pathway to the macroline-type indole alkaloids, talcarpine and alstonerine from ajmaline

Ajmaline (6) was transformed into two macroline-related indole alkaloids, talcarpine (1) and alstonerine (2) via the common synthetic intermediate (13). The stereochemistry at C19 position in talcarpine (1) and talpinine (5) were elucidated by NOE experim