Enantioselective synthesis of naturally occurring isoquinoline alkaloids: (S)-(−)-trolline and (R)-(+)-oleracein E
Literature Information
Publication Date
2017-03-06
DOI
10.1039/C7QO00062F
Impact Factor
5.281
Authors
Weilong Lin
View Original
Abstract
The highly efficient asymmetric syntheses of a pair of enantiomers, (S)-(−)-trolline and (R)-(+)-oleracein E, from commercially available 2-methyl-3-butyn-2-ol, benzaldehyde and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline have been achieved in five steps with the catalytic enantioselective C1-alkynylation of 6,7-dimethoxy-3,4-dihydroisoquinoline as a key step, providing an efficient general approach for this type of naturally occurring chiral isoquinoline alkaloids.
Related Literature
Specificity of metal ion cross-linking in marine mussel adhesives
Jennifer Monahan, Jonathan J. Wilker
2003-06-09
Communication
DOI: 10.1039/B301052J
Cross-metathesis reactions of vinyl-chlorins and -porphyrins catalyzed by a “second generation” Grubbs' catalyst
Xin Liu, Ethan Sternberg, David Dolphin
2004-02-27
Communication
DOI: 10.1039/B400001C
Lactone synthesis activity in a site-directed mutant of an extradiol catechol dioxygenase enzyme
Sharon Mendel, Andrew Arndt, Timothy D. H. Bugg
2004-12-14
Communication
DOI: 10.1039/B414292F
Fluorescence enhancement of a signaling system in the simultaneous presence of transition and alkali metal ions: a potential AND logic gate
Bamaprasad Bag, Parimal K. Bharadwaj
2004-12-03
Communication
DOI: 10.1039/B413274B
Intramolecular inclusion in novel octaester cavitands
Eric Efrain Dueno, Kirpal S. Bisht
2004-03-11
Communication
DOI: 10.1039/B316498E
Synthesis of a β-diiminate iridium tetrahydride for arene C–H bond activation
Wesley H. Bernskoetter, Emil Lobkovsky, Paul J. Chirik
2004-02-27
Communication
DOI: 10.1039/B315817A
Photoassisted oxygenation of alkane catalyzed by ruthenium complexes using 2,6-dichloropyridine N-oxide under visible light irradiation
Motowo Yamaguchi, Takashi Kumano, Dai Masui, Takamichi Yamagishi
2004-02-23
Communication
DOI: 10.1039/B316970G
Synthetic control of ordered and disordered arrays of carbon nanofibers from SBA-15 silica templates
Suk Bon Yoon, Jeong Yeon Kim, Fathi Kooli, Chul Wee Lee, Jong-Sung Yu
2003-06-18
Communication
DOI: 10.1039/B304227H
Backbone-extended pyrrolidinepeptide nucleic acids (bepPNA): design, synthesis and DNA/RNA binding studies
T. Govindaraju, Vaijayanti A. Kumar
2004-12-02
Communication
DOI: 10.1039/B413542C
Surface recognition of biomacromolecules using nanoparticle receptors
Ayush Verma, Vincent M. Rotello
2004-12-08
Feature Article
DOI: 10.1039/B410889B
You might also like
Compound Q&A
What precautions should be taken when handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3)?
When handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3), safety go...
40716-16-34-Methyl-6-(trifluor...
Compound Q&A
What is 4-(3,5-Difluorophenyl)aniline (CAS: 405058-00-6)?
4-(3,5-Difluorophenyl)aniline is an aromatic organic compound with the CAS numbe...
405058-00-64-(3,5-Difluoropheny...
Compound Q&A
How is 5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid (CAS: 338982-07-3) typically synthesized?
5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid can ...
338982-07-35-{[4-(Trifluorometh...
Compound Q&A
What is the market or research trend for 4-Benzylaniline hydrochloride (CAS: 6317-57-3)?
The market for 4-Benzylaniline hydrochloride (CAS: 6317-57-3) is steadily growin...
6317-57-34-Benzylaniline hydr...
Compound Q&A
Is [3-(Diethylsulfamoyl)phenyl]boronic acid (CAS: 871329-58-7) safe?
[3-(Diethylsulfamoyl)phenyl]boronic acid is generally considered safe when handl...
871329-58-7[3-(Diethylsulfamoyl...
Compound Q&A
What are the main uses of 3-Bromo-2,5-dimethoxyaniline (CAS: 115929-62-9)?
3-Bromo-2,5-dimethoxyaniline is mainly used in the pharmaceutical and chemical i...
115929-62-93-Bromo-2,5-dimethox...
Compound Q&A
What regulatory guidelines apply to N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7)?
N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7) is subject to ...
915922-67-7N-Methyl-1-(5-methyl...
Compound Q&A
What industries use Carbamic acid, N-[(5S)-5,6-diamino-6-oxohexyl]-, 1,1-dimethylethyl ester (CAS: 24828-96-4)?
This compound is primarily used in the pharmaceutical industry for the synthesis...
24828-96-4Carbamic acid, N-[(5...
Compound Q&A
How should 2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) be stored?
2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) sho...
1298101-47-92-Methyl-2-propanyl ...
Compound Q&A
What industries use Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9)?
Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9) is utilized in the pharma...
367-33-9Ethyl 2-bromo-4,4,4-...
Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide structure](https://static.chemtradehub.com/structs/142/1426944-49-1-1e4c.webp "N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide structure")
N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide
CAS Number:
1426944-49-1
Molecular Formula:
C25H28ClN3O
![2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraen-1-yloxy]-1,3-propanediol structure](https://static.chemtradehub.com/structs/222/222723-55-9-0348.webp "2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraen-1-yloxy]-1,3-propanediol structure")
2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraen-1-yloxy]-1,3-propanediol
CAS Number:
222723-55-9
Molecular Formula:
C23H40O3
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.