Novel tocopherol compounds XI. Synthesis, bromination and oxidation reactions of 3-(5-tocopheryl)propionic acid

Authors
Rosenau, T Habicher, WD Potthast, A Kosma, P
Citation
T. Rosenau et al., Novel tocopherol compounds XI. Synthesis, bromination and oxidation reactions of 3-(5-tocopheryl)propionic acid, SYNLETT, (3), 1999, pp. 291-294
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
3
Year of publication
1999
Pages
291 - 294
Database
ISI
SICI code
0936-5214(199903):3<291:NTCXSB>2.0.ZU;2-C
Abstract
3-(5-Tocopheryl)propionic acid (gamma-tocopherol-5-propionic acid, 13) has been synthesized by a multi-step sequence involving the hetero-Diels-Alder reaction between O-methyl-C,O-bis-(trimethylsilyl)ketene acetal (10) and th e ortho-quinone methide of alpha-tocopherol (5) as the key step. The title compound is the first 5a-substituted tocopherol that shows an oxidation beh avior largely similar to alpha-tocopherol.