Construction of C2-indolyl-quaternary centers by branch-selective allylation: enabling concise total synthesis of the (±)-mersicarpine alkaloid
Literature Information
Publication Date
2023-12-18
DOI
10.1039/D3SC04732F
Impact Factor
9.825
Authors
Minakshi Ghosh, Samrat Sahu, Shuvendu Saha, Modhu Sudan Maji
View Original
Abstract
Herein we report a branch-selective allylation strategy for accessing C2-indolyl-all-carbon quaternary centers using allylboronic acids. This approach boasts broad functional group tolerance, scalability, and relies on easily accessible allyl alcohol precursors. Importantly, the C3-position of the indole remains free, offering a handle for further synthetic refinement. Mechanistic pathways, corroborated by density functional theory (DFT), suggest the involvement of an indolenine intermediate and a Zimmerman–Traxler-like transition state during allylboration. Demonstrating its efficacy, the method was applied to the total synthesis of the (±)-mersicarpine alkaloid and enabled formal synthesis of additional alkaloids, such as (±)-scholarisine G, (±)-melodinine E, and (±)-leuconoxine.
Related Literature
Abinitio calculations and matrix infrared spectra of the nitrous acid complexes with HF and HCl
Paper
DOI: 10.1039/A900704K
Mixed micelles of n-alkyltrimethylammonium bromides: influence of alkyl chain length
Paper
DOI: 10.1039/A903532J
How large should proteins be? The minimal size of a good structure seeker
Paper
DOI: 10.1039/A903594J
Solubilities and solubilisation enthalpies of alkali metal uranates(VI) in carbonate melts
Paper
DOI: 10.1039/A902615K
You might also like
Compound Q&A
What is 3-Fluoro-2-methylbenzylamine (CAS: 771573-36-5)?
3-Fluoro-2-methylbenzylamine is an organic compound with the CAS number 771573-3...
771573-36-53-Fluoro-2-methylben...
Compound Q&A
Is Tert-butyl 2-(oxetan-3-ylidene)acetate (CAS: 1207175-03-8) safe?
Tert-butyl 2-(oxetan-3-ylidene)acetate is considered safe for its intended uses ...
1207175-03-8Tert-butyl 2-(oxetan...
Compound Q&A
What precautions should be taken when handling 4-Acetyl-2-fluorobenzonitrile (CAS: 214760-18-6)?
Proper personal protective equipment (PPE) such as gloves, goggles, and a lab co...
214760-18-64-Acetyl-2-fluoroben...
Compound Q&A
How is 2-Ethyl-4-methyl-1,3-thiazole (CAS: 15679-12-6) typically synthesized?
2-Ethyl-4-methyl-1,3-thiazole is commonly synthesized via the reaction of thiour...
15679-12-62-Ethyl-4-methyl-1,3...
Compound Q&A
How should 5',5''-([2,2'-Bithiophene]-5,5'-diyl)bis(([1,1':3',1''-terphenyl]-4,4''-dicarboxylic acid)) (CAS: 1227780-71-3) be stored?
This compound should be stored in a cool, dry place away from direct sunlight an...
1227780-71-35',5''''-([2,2'-Bith...
Compound Q&A
What regulatory guidelines apply to L-Lysine Acetate Salt (CAS: 52315-92-1)?
L-Lysine Acetate Salt (CAS: 52315-92-1) is subject to various regulatory guideli...
52315-92-1L-LYSINE ACETATE SAL...
Compound Q&A
Is 6-Fluoro-3-hydroxy-2-pyrazinecarboxamide (CAS: 259793-96-9) safe?
6-Fluoro-3-hydroxy-2-pyrazinecarboxamide (CAS: 259793-96-9) is generally conside...
259793-96-96-Fluoro-3-hydroxy-2...
Compound Q&A
What are the physical and chemical properties of 1,1'-Sulfonylbis(1H-imidazole) (CAS: 7189-69-7)?
1,1'-Sulfonylbis(1H-imidazole) is a crystalline solid with a molecular weight of...
7189-69-71,1'-Sulfonylbis(1H-...
Compound Q&A
What industries use 4-methyl-7-nitro-1H-indole-3-carbonitrile (CAS: 289483-82-5)?
4-Methyl-7-nitro-1H-indole-3-carbonitrile (CAS: 289483-82-5) is primarily used i...
289483-82-54-methyl-7-nitro-1H-...
Compound Q&A
How should waste containing 5-Bromo-3-indolyl-beta-galactoside (CAS: 97753-82-7) be handled?
Waste containing 5-Bromo-3-indolyl-beta-galactoside (CAS: 97753-82-7) should be ...
97753-82-75-Bromo-3-indolyl-be...
Source Journal
Chemical Science
CiteScore:
14.4
Self-citation Rate:
3.9%
Articles per Year:
1413
Our journal has a wide-ranging scope which covers the full breadth of the chemical sciences. The research we publish contains the sorts of novel ideas, challenging questions and progressive thinking that bring undiscovered breakthroughs within reach. Your paper could focus on a single area, or cross many. It could be beyond the accepted bounds of the chemical sciences. It might address an immediate challenge, contribute to a future breakthrough or be wholly conceptual. We’re a team from every field of the chemical sciences, and know from experience that breakthroughs that drive the solutions to global challenges can come from anywhere, at any time. You could even start an entirely new area of research. Too bold? Too progressive? No such thing
Recommended Compounds
3,3'-(Piperazine-1,4-diyl)bis(2-hydroxypropane-1-sulfonic acid) Sodium Salt
CAS Number:
108321-08-0
Molecular Formula:
C20H41N4Na3O16S4
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.