Brief, efficient and highly diastereoselective synthesis of (±)-pumiliotoxin C based on the generation of an octahydroquinoline precursor via a four-component reaction
Literature Information
Publication Date
2011-05-06
DOI
10.1039/C1CC11246E
Impact Factor
6.222
Authors
Swarupananda Maiti, J. Carlos Menéndez
View Original
Abstract
A short and highly diastereoselective synthesis of the amphibian alkaloid pumiliotoxin C is described, based on the preparation of an octahydroquinoline derivative through a four-component reaction. The route proceeds in 66% overall yield from 1,3-cyclohexanedione and includes two hydrogenation steps, whose stereochemical outcome was controlled vianitrogen acylation.
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Source Journal
Chemical Communications
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Recommended Compounds
4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine
CAS Number:
485799-04-0
Molecular Formula:
C15H23BN2O3
![N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure](https://static.chemtradehub.com/structs/480/480452-37-7-0898.webp "N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure")
N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide
CAS Number:
480452-37-7
Molecular Formula:
C16H22ClN5O3
![N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine structure](https://static.chemtradehub.com/structs/238/2387704-62-1-25f4.webp "N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine structure")
N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine
CAS Number:
2387704-62-1
Molecular Formula:
C21H20Cl2N10O
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