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.
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Chemical Science
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Recommended Compounds
3,3'-(Piperazine-1,4-diyl)bis(2-hydroxypropane-1-sulfonic acid) Sodium Salt
CAS Number:
108321-08-0
Molecular Formula:
C20H41N4Na3O16S4
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5-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)-2H-pyrazolo[3,4-c]pyridazin-3-amine
CAS Number:
865362-74-9
Molecular Formula:
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![(3R)-3-(3-Fluorophenyl)-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)propanoic acid structure](https://static.chemtradehub.com/structs/500/500789-04-8-20dd.webp "(3R)-3-(3-Fluorophenyl)-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)propanoic acid structure")
(3R)-3-(3-Fluorophenyl)-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)propanoic acid
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Molecular Formula:
C14H18FNO4
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