34384-65-1

Upstream product

• 92138-22-2 Anthirinal 
• 61-54-1 tryptamine 
• 74447-13-5 (S)-3-((R)-4-Oxo-6,10-dithia-spiro[4.5]dec-2-yl)-dihydro-furan-2-one 
• 84573-43-3 Cyanomethyl-dimethyl-[(E)-3-((R)-3-oxo-cyclopentyl)-allyl]-ammonium; bromide 
• 109755-63-7 C₂₀H₃₆O₅S₂Si 
• 97456-74-1 2-Dimethylamino-3-((R)-3-oxo-cyclopentyl)-pent-4-enenitrile 
• 84573-42-2 (3R)-<3-bromo-(E)-prop-1-enyl>cyclopentanone 
• 82167-09-7 (3R)-<3-hydroxy-(E)-prop-1-enyl>cyclopentanone 
• 97456-79-6 (3S,4R)-N-<2-(3-indolyl)ethyl>-3-(propane-1,3-dithio)ethyl-4-tert-butyldimethylsilyloxymethyl-5-hexenamide 
• 97456-78-5 (3S)-(propane-1,3-dithio)ethyl-4-tert-butyldimethylsilyloxymethyl-5-hexenoic acid 
• 97456-80-9 (4S)-(tert-butyldimethylsilyloxymethyl-prop-2-enyl)-2,2-(propane-1,3-dithio)cyclopentanone 
• 97456-77-4 (3R)-(1-tert-butyldimethylsilyloxymethyl-prop-2-enyl)cyclopentanone 
• 97456-76-3 (3R)-(1-tert-butyldimethylsilyloxymethylprop-2-enyl)cyclopentanol 
• 97456-72-9 (1'S,2R,12bRS)-2-(1-hydroxymethyl-prop-2-enyl)-1,2,3,4,6,7,12,12b-octahydro-4-oxoindolo<2,3-a>-quinolizine 

Downstream Products

• 16049-29-9 18,19-Dihydroantirhine 
• 16049-29-9 Dihydroantirhin 

Relevant academic research and scientific papers

General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers

A general synthetic strategy for antirhine alkaloids was developed in this study. The cyanide-catalyzed imino-Stetter reaction of ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde afforded the corresponding indole-3-acetic acid derivative. Subsequent formation of the six-membered C ring followed by trans-selective installation of the two-carbon unit at C-15 provided rapid access to the key intermediate. Stereoselective installation of substituents at C-20 allowed the total syntheses of (±)-antirhine, (±)-18,19-dihydroantirhine, and their 20-epimers, all of the known natural products in the antirhine family.

A Highly Enantioselective Synthesis of (-)-Antirhine by Chemo-Enzymatic Approach

(-)-Antirhine 2 was synthesized in an efficient and stereocontrolled fashion from the readily available (1R-2S)-cyclohexene dimethanol monoacetate 6.A key step was the regio- and stereoselective Pictet Spengler cyclization of the masked dialdehyde 12 to t

TOTAL SYNTHESIS OF (-)-ANTIRHINE

Total synthesis of (-)-antirhine (6) has been achieved from a potentially useful chiral synthon, (3S)-cyclopentanone (1), via β,γ-unsaturated aldehyde (5), which was obtained by mild hydrolysis of α-cyano-N,N-dimethylaminocyclopentanone (7).

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.