Synthesis of the α-Tocopheramine-15N Model Compound 2,2,5,7,8- Pentamethyl-6-chromanylamine-15N

Stefan      Bohmdorfer; Lars      Gille; Thomas      Rosenau

doi:10.2174/157017810791130612

Abstract

2,2,5,7,8-Pentamethyl-6-chromanylamine-15N was prepared by condensation of ZnCl2-catalyzed condensation of 2,3,5-trimethylphenol with isoprene, followed by conversion of the resulting chroman into the 6-nitro-derivative and further reduction to the title compound, which possesses a 2-methyl group instead of the isoprenoid side chain of tocopherols and tocopheramines. Tocopheramines and their short-chain analogues are current targets in medicinal chemistry and anti-cancer research.

Keywords: Tocopherols, tocopheramine, vitamin E, isotopic labeling, chromans

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Letters in Organic Chemistry

Title: Synthesis of the α-Tocopheramine-15N Model Compound 2,2,5,7,8- Pentamethyl-6-chromanylamine-15N

Volume: 7 Issue: 4

Author(s): Stefan Bohmdorfer, Lars Gille and Thomas Rosenau

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Keywords: Tocopherols, tocopheramine, vitamin E, isotopic labeling, chromans

Abstract: 2,2,5,7,8-Pentamethyl-6-chromanylamine-15N was prepared by condensation of ZnCl2-catalyzed condensation of 2,3,5-trimethylphenol with isoprene, followed by conversion of the resulting chroman into the 6-nitro-derivative and further reduction to the title compound, which possesses a 2-methyl group instead of the isoprenoid side chain of tocopherols and tocopheramines. Tocopheramines and their short-chain analogues are current targets in medicinal chemistry and anti-cancer research.

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Bohmdorfer Stefan, Gille Lars and Rosenau Thomas, Synthesis of the α-Tocopheramine-15N Model Compound 2,2,5,7,8- Pentamethyl-6-chromanylamine-15N, Letters in Organic Chemistry 2010; 7 (4) . https://dx.doi.org/10.2174/157017810791130612