
%0 Journal Article
%A Suarna, Cacang 
%A Dean, Roger T. 
%A Southwell-Keely, Peter T. 
%T Synthesis of &#945;-Tocopherol Analogues
%J Australian Journal of Chemistry
%D 1998/02/05
%V 50
%N 12
%P 1129-1136
%K 
%R https://doi.org/10.1071/C97044
%U https://www.publish.csiro.au/paper/C97044 
%X A range of a-tocopherol analogues of varying side-chain length and structure has been prepared by the Wittig reaction of alkyltriphenylphosphonium bromides with either 6-benzyloxy-2,5,7,8-tetramethylchroman- 2-carbaldehyde (8) or 6-acetoxy-2,5,7,8-tetramethylchroman-2-carbaldehyde (14). These analogues include 2-hexyl-2,5,7,8-tetramethylchroman-6-ol (11), 2-heptyl-2,5,7,8-tetramethylchroman-6-ol (12) and 2,5,7,8-tetramethyl-2-(pent-1-enyl)chroman-6-ol (15). Methoxycarbonylmethyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate (2) was formed by reaction of the triethylammonium salt of trolox (1) with methyl bromoacetate. Reaction of methoxycarbonylmethyltriphenylphosphonium bromide (16) with (8) did not produce the expected methyl 3-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)prop-2-enoate (17), but rather 4-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl)but-3-en-2-one (22). A proposed mechanism for this unusual reaction is discussed. 
