23172-92-1

Upstream product

• 73748-86-4 Gardneral 
• 23172-92-1 gardnerine 
• 73748-86-4 gardneral 
• 73748-86-4 16-epigardneral 
• 355840-03-8 6-methoxy-D-tryptophan ethyl ester 
• 854931-43-4 trans-(1S,3R)-(-)-2-benzyl-3-ethoxycarbonyl-7-methoxy-1-methoxycarbonylethyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 
• 854931-46-7 C₁₉H₂₁IN₂O₂ 
• 854931-44-5 C₂₂H₂₂N₂O₂ 
• 854931-47-8 3-ethylidene-10-methoxy-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-one 
• 854931-42-3 2-benzylamino-3-(6-methoxy-1H-indol-3-yl)-propionic acid ethyl ester 
• 854931-45-6 C₁₅H₁₆N₂O₂ 
• 23172-98-7 gardnutine 
• 854931-48-9 3-ethylidene-10-methoxy-13-methylene-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine 

Downstream Products

• 23172-92-1 16-epigardnerine 
• 23172-98-7 gardnutine 
• 23172-97-6 (16S)-7,17-epoxy-11-methoxy-(7β)-7H-sarpagane 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of Sarpagine-Related Indole Alkaloids Hydroxygardnerine, Hydroxygardnutine, Gardnerine, (E)-16-epi-Normacusine B, and Koumine

Sarpagine-related indole alkaloids (-)-hydroxygardnerine, (+)-hydroxygardnutine, (-)-gardnerine, (+)-(E)-16-epi-normacusine B, and (-)-koumine were divergently synthesized via a common intermediate possessing a piperidine ring with an exocyclic (E)-ethylidene side chain, which was constructed by a gold(I)-catalyzed 6-exo-dig cyclization strategy.

General approach for the synthesis of 12-methoxy-substituted sarpagine indole alkaloids including (-)-12-methoxy-Nb-methylvoachalotine, (+)-12-methoxy-Na-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline

The enantiospecific synthesis of 7-methoxy-D-tryptophan ethyl ester was completed by combination of the Larock heteroannulation process with a Schoellkopf-based chiral auxiliary in good yield. This ester was then employed in the first regiospecific, stere

First regiospecific, enantiospecific total synthesis of gardnerine and gardnutine

The first enantiospecific total synthesis of gardnerine and gardnutine has been achieved from 6-methoxy-d-tryptophan via the asymmetric Pictet-Spengler reaction, a stereocontrolled intramolecular enolate driven palladium-mediated cross-coupling reaction a

STRUCTURE OF PELIRINE AND CHEMICAL CONVERSION OF GARDNERINE TO 11-METHOXY-16-EPIAFFININE

The structure of pelirine, isolated from roots of Rauwolfia perakensis was shown to be 10-methoxyepiaffinine by comparison with the spectral data of 11-methoxyepiaffinine which was synthesized from the known alkaloid gardnerine.The proposed structure has been confirmed by X-ray crystallography.

CHARACTERISTICS OF VELLOSIMINE REDUCTASE, A SPECIFIC ENZYME INVOLVED IN THE BIOSYNTHESIS OF THE RAUWOLFIA ALKALOID SARPAGINE

A plant enzyme - vellosimine reductase - has been isolated from Rauwolfia cell suspension cultures.This new enzyme has been purified (110-fold) and characterized.The reductase is a specific enzyme of the sarpagine pathway catalyzing the NADPH dependent conversion of vellosimine into 10-deoxysarpagine.The latter alkaloid is the immediate biogenetic precursor of sarpagine as shown by its high in vivo incorporation rate (86percent) into sarpagine.