16049-28-8

Usage

Uses

Used in Pharmaceutical Research:
(2S,βR)-β-Vinyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-2-ethanol is used as a research compound for exploring its potential pharmacological activities. Its unique structure and properties make it a candidate for further studies to understand its interactions with biological systems and its possible therapeutic applications.
Used in Drug Development:
In the field of drug development, (2S,βR)-β-Vinyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-2-ethanol is utilized as a lead compound for the design and synthesis of new pharmaceutical agents. Its structural features may offer advantages in targeting specific biological pathways or receptors, potentially leading to the development of novel therapeutics for various diseases.
Used in Medicinal Chemistry:
(2S,βR)-β-Vinyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-2-ethanol serves as a valuable tool in medicinal chemistry for the synthesis of related analogs and derivatives. By modifying its structure, chemists can investigate structure-activity relationships and optimize its pharmacological properties, enhancing its potential as a therapeutic agent.
Note: Since the provided materials do not specify particular applications or industries for (2S,βR)-β-Vinyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-2-ethanol, the uses listed above are general and based on the compound's potential properties and characteristics. Further research and studies would be necessary to identify specific applications and industries where (2S,βR)-β-Vinyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-2-ethanol could be effectively utilized.

InChI:InChI=1/C19H24N2O/c1-2-13(12-22)14-7-9-21-10-8-16-15-5-3-4-6-17(15)20-19(16)18(21)11-14/h2-6,13-14,18,20,22H,1,7-12H2/t13-,14-,18-/m0/s1

Upstream product

• 92138-22-2 Anthirinal 
• 137171-66-5 (R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol 
• 61-54-1 tryptamine 
• 80758-91-4 (4R)-4-allyldihydrofuran-2(3H)-one 
• 81525-21-5 (3R,4R)-3,4-Diallyl-dihydro-furan-2-one 
• 81525-32-8 (2R,3S)-2-Allyl-3-cyanomethyl-hex-5-enoic acid 
• 81525-23-7 (S)-3-((R)-2-Oxo-tetrahydro-furan-3-yl)-hex-5-enenitrile 
• 81525-33-9 (S)-4-((R)-1-Hydroxymethyl-allyl)-1-[2-(1H-indol-3-yl)-ethyl]-piperidin-2-one 
• 84573-42-2 (3R)-<3-bromo-(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 

Downstream Products

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

Relevant academic research and scientific papers

Hydrolysis and Selective Reduction with Yeast: Enantiospecific Synthesis of Antirhine from Secologanin

Glucoside hydrolysis and chemoselective reduction of secologanin ethylene acetal 2 with baker's yest affords a C-1 reduced aglucone 4 from which (+)-antirhine 8 is obtained in a four-step sequence.

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.

Biomimetic synthesis of monoterpenoid indole alkaloids from aglucones of secologanin derivatives: pH controlled product selectivity

Variation of the pH for hydrolysis of secologanin derivatives with β-glucosidase controls rearrangement of the aglucone to afford different products, and hence stercoselective syntheses of heteroyohimbine, yohimbine and Aspidosperma-type alkaloids; with baker's yeast chemoselective reduction can also be achieved to give a precursor for antirhine and related alkaloids.

Enantio- and stereocontrolled synthesis of (-)-semburin, (+)-N-benzoylmeroquinene aldehyde, (-)-antirhine, and (+)-isocorynantheol from common (+)-norcamphor

A general enantio- and stereocontrolled route to the representative secologanin natural products, (-)-semburin, (+)-N-benzoylmeroquinene aldehyde, (-)-antirhine, and (+)-isocorynantheol, has been developed starting from (+)-norcamphor as a common chiral b

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

Carbohydrates in total synthesis of (-)-antirhine

Amide 5 was obtained by condensation between pyranose 3 and tryptamine 4; in few steps, the indoloquinolizidine 13a was prepared with a perfect stereocontrol of the 2β-H configuration; total synthesis of (-)-antirhine 2 was then achieved from 13a.

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.

Synthesis of a Potential Synthon for the Chiral Synthesis of the Corynanthe-type Indole Alkaloids: Enantioselective Total Synthesis of (-)-Antirhine

The chiral formylmethyl(vinyl)tetrahydropyranone (16), a potential versatile synthon for the chiral synthesis of the Corynanthe-type indole alkaloids, has been synthesised and converted into (-)-antirhine, the major alkaloid of Antirhea putaminosa (F.Muel