38990-08-8

Usage

Uses

Used in Pharmaceutical Industry:
(20β)-20,21-Dihydro-21-methyl-18-noralstphyllan-19-al is used as a pharmaceutical compound for its potential therapeutic applications. As a carboline alkaloid, it may possess various biological activities that can be harnessed for the development of new drugs or treatments.
Used in Chemical Research:
(20β)-20,21-Dihydro-21-methyl-18-noralstphyllan-19-al is also used in chemical research as a starting material or intermediate for the synthesis of other complex organic molecules. Its unique structure and properties make it a valuable tool for understanding the chemical behavior of similar compounds and for exploring new synthetic pathways.
Used in Natural Product Extraction:
(20β)-20,21-Dihydro-21-methyl-18-noralstphyllan-19-al is used in the extraction and purification of natural products from plant sources. Its presence in the stem bark of Pleiocarpa talbotii Wernham makes it an important marker compound for the identification and characterization of this plant's bioactive constituents.

References

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

Upstream product

• 133761-72-5 C₂₂H₂₈N₂O₂ 
• 67-56-1 methanol 
• 219584-19-7 N_b-benzyltalcarpine 
• 16101-12-5 macrocarpine A 
• 219584-15-3 N_b-benzyl, N_b-21-secotalpinine 
• 219584-13-1 C₂₈H₃₂N₂O₂ 
• 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 
• 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 
• 219584-09-5 C₂₇H₃₀N₂O 
• 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 
• 219584-05-1 C₂₇H₃₂N₂O₂ 
• 133761-70-3 C₂₁H₂₈N₂O₂ 
• 133761-71-4 C₂₈H₃₄N₂O₂Se 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

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.

Unusual spirocyclic macroline alkaloids, nitrogenous derivatives, and a cytotoxic bisindole from Alstonia

The bark extract of the Malayan A. macrophylla provided several novel indoles with unprecedented carbon skeletons, an unusual nitrogenous compound, a cytotoxic bisindole, several new macroline alkaloids, in addition to other known alkaloids. The structures of the new compounds were established by spectroscopic analysis.

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