16146-60-4Relevant academic research and scientific papers
Synthesis of α-tocopherol analogs with unsaturated side chain and their transformation into the corresponding chromans with ω-functionalized side chain
Odinokov,Spivak,Emelianova,Kutepov,Khalilov
, p. 2227 - 2230 (2001)
α-Tocopherol analogs with double bond-containing side chains were synthesized by condensation of trimethylhydroquinone with optically active (3R/S,4S)-3,4,8-trimethylnona1,7-dien-3-ol and linalool in the presence of the zeolite-containing Tseokar-10 aluminosilicate. Ozonolysis of these compounds gave the corresponding chromans with ω-formyl or (after hydride reduction) ω-hydroxyl groups in the side chain.
A Convenient access to (All-rac)-α-tocopherol acetate from linalool and dihydromyrcene
Gembus, Vincent,Sala-Jung, Nathalie,Uguen, Daniel
experimental part, p. 829 - 842 (2009/12/25)
Refluxing trimethylhydroquinone 2 in 10:1 dodecane/CH2Cl 2 with linalool 3b (two-fold excess) and camphorsulfonic acid, then treating the crude condensation product (consisting of a mixture of the chromanols 1b and 1c, alongside the tricyclic compounds 9 and 10) sequentially with Ac2O and m-CPBA afforded, after removal by column chromatography of the 9/10 acetates, a mixture of the regioisomeric epoxides 1jOAc and 1kOAc (ratio 9:1, total 60%). Treatment of this mixture with Al(O-i-Pr)3 followed by CuI-catalysed Wurtz coupling of the acetates of the resulting allylic alcohols with citronellylmagnesium chloride 12a, and finally hydrogenation then provided the title acetate (overall 46% from 2).
Synthesis of α-tocopherol and naphthotocopherol analogs with a carboxyl group in the side chain
Spivak,Knyshenko,Mallyabaeva,Odinokov
, p. 306 - 311 (2007/10/03)
On the basis of ozonolysis of short-chain α-tocopherol and naphthotocopherol analogs with a terminal isopropylidene group in the side chain, a general approach to the synthesis of 6-hydroxy-2,5,7,8- tetrtamethylchroman-2-yl-and 6-hydroxy-2,5-dimethyl-3,4-
