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Biomimetic Chromanol Cyclisation: A Common Route to α‐Tocotrienol and α‐Tocopherol
Author(s) -
Chapelat Julien,
Chougnet Antoinette,
Woggon WolfD.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900019
Subject(s) - tocotrienol , chemistry , tocopherol , double bond , stereochemistry , protonation , covalent bond , ring (chemistry) , dipeptide , chirality (physics) , organic chemistry , antioxidant , peptide , biochemistry , vitamin e , chiral symmetry , ion , physics , quantum mechanics , nambu–jona lasinio model , quark
A common synthetic route to α‐tocotrienol and α‐tocopherol has been accomplished by a biomimetic cyclisation that yields the chromanol ring. The chirality at C2 of the chromanol was induced by a covalently attached chiral dipeptide. Its terminal Asp participates in the enantioface‐selective protonation of the double bond of the α‐tocotrienol precursor.α‐Tocotrienol was diastereoselectively hydrogenated toα‐tocopherol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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