- Novel tocopheryl compounds. Part 15: One-pot formation of furotocopheryl derivatives
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Reaction of tocopheryl bromide 2a or chromanyl bromide 2b with triphenyl phosphine produced phosphomium salt intermediates (3a-b), which further reacted with acyl chlorides to novel furotocopherol compounds 4-11 in good yields. The cyclization proceeded according to a two step esterification-Wittig mechanism. Similarly, furotocopheryl dimer 12 was prepared starting from oxalyl chloride. The coupling of tocopheryl phosphonium salt 3a onto modified polystyrene provided a new, vitamin E-loaded resin.
- Adelw?hrer, Christian,Rosenau, Thomas,Binder, Wolfgang H.,Kosma, Paul
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Read Online
- Hybrid-increased radical-scavenging activity of resveratrol derivatives by incorporating a chroman moiety of vitamin e
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A winning combination: Resveratrol derivatives incorporating a chroman moiety of vitaminE were constructed, resulting in the remarkable enhancement in tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl radical (HNTTM)-scavenging activity as compared with the parent molecules (see scheme). Reaction kinetic analysis, oxidative product identification, and redox potential determination demonstrate that the reaction is governed by a sequential proton-loss electron-transfer (SPLET) mechanism.
- Yang, Jie,Liu, Guo-Yun,Lu, Dong-Liang,Dai, Fang,Qian, Yi-Ping,Jin, Xiao-Ling,Zhou, Bo
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supporting information; experimental part
p. 12808 - 12813
(2011/02/22)
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- Diversity-oriented synthesis of furo[3,2-f]chromanes with antimycobacterial activity
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We previously reported the synthesis and the antimycobacterial activity of 4-(7,7-dimethyl-7H-furo[3,2-f]chromen-2-yl)pyridine. From this result, we sought to design simple synthetic accesses to related structures allowing the preparation of a diverse set
- Alvey, Luke,Prado, Soizic,Saint-Joanis, Brigitte,Michel, Sylvie,Koch, Michel,Cole, Stewart T.,Tillequin, Francois,Janin, Yves L.
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experimental part
p. 2497 - 2505
(2009/09/30)
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- Synthesis of 5a-α-tocopheryl azide and its reaction to 1-(5a-α-tocopheryl)-1,2,3-triazols by [2+3]-cycloaddition
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1,2,3-Triazoles with 1-position substituents, derived from α-tocopherol (vitamin E), were synthesized by 1,3-dipolar cycloaddition reactions of 5a-azido-α-tocopheryl acetate with alkynes, and were fully analytically characterized. NMR spectra of the compounds and crystal structures of derivatives with a truncated isoprenoid side chain are presented. The tocopheryl moiety is readily cleaved in basic media, as a prerequisite for the use in delivery systems showing pH-dependent drug release. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Adelwoehrer, Christian,Rosenau, Thomas,Kloser, Elisabeth,Mereiter, Kurt,Netscher, Thomas
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p. 2081 - 2086
(2007/10/03)
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