Vitamin E synthesis

Tietze, L.F. and Gorlitzer, J., Preparation of chiral building blocks for a highly convergent vitamin E synthesis. Systematic investigations on the enantioselectivity of the Sharpless bishydroxilation. Synthesis, 1998, 873. 

Mercier, C. and Chabardes, P. (1995) Organometallic chemistry in industrial vitamin A and vitamin E synthesis. Chem. Ind. (Dekker) Catal. Org. React., 62, 213. Fremy, G., Castanet, Y., Grzybek, R., Monflier, E., Mortreux, A., Trzedak, A.M. and Ziolkowski, J.J. (1995) A new, highly selective, water-soluble rhodium catalyst for methyl acrylate hydroformylation. /. Organomet. Chem., 505, 11. 

Trimethyl phenol, a key intermediate for vitamin E synthesis, is made from m-cresol and is easily the largest derivative of m-cresol. 

Similar results were observed with other allylic alcohols. This rearrangement was used to obtain the optically active Ci4-carbon unit 3, which is an important intermediate in vitamin E synthesis, originally prepared from natural phytol. 

The rearrangement of 3,5,5-trimethylcyclohex-2-ene-l,4-dione to trimethylhy-droquinone, an intermediate in vitamin E synthesis, can be accomplished over HY-zeolite in the presence of hydrogen (Hoelderich et al., 1988). 

TRANSITION METAL CATALYZED REACTIONS OF CARBENES 2) Vitamin E synthesis [102a]. 

Type 0. Type-0 production as a supplementary case occurs even in resting cells that use only a little substrate for their own metabolism. The microbial cells function only as enzyme carriers. Steroid transformation and vitamin E synthesis by Saccharomyces cerevisiae are examples. 

Vitamin E (a) L. F. Tietze, J. Gorlitzer, A. Schuffenhauer, M. HUbner, Eur. J. Org. Chem. 1999, 1075-1084. Enantioselective synthesis of the chromane moiety of vitamin E. (b) L. F. Tietze, J. Gorlitzer, Synlett 1997, 1049-1050. Preparation of enantiopure precursors for the vitamin E synthesis. A comparison of the asymmetric allylation of ketones and the sharpless bishydroxylation. (+)-Hydroxymyoporone (c) L. F. Tietze, C. Wegner, C. Wulff, Chem.-Eur. J. 1999, 5, 2885-2889. First total synthesis and determination of the absolute configuration of the stress factor (+)-hydroxymyoporone. 5,6-Dihydrocineromycin B (d) L. F. Tietze, L. Vblkel, Angew. Chem. Int. Ed. 2001, 40, 901-902. Total synthesis of the macrolide antibiotic 5,6-dihydrocineromycin B. 

The general biochemistry of vitamin E has been extensively reviewed (Azzi and Stocker, 2000 Brigelius Flohe and Traber, 1999 Stone and Papas, 1997). This review will primarily focus on the biochemical and health aspects of vitamin E in food. It is important, however, to contrast the chemical forms of vitamin E found in plants with that found in mammals and in dietary supplements. Vitamin E is often equated with a-tocopherol, which is the primary lipid-soluble antioxidant in human plasma, and the most potent form in protecting the fetuses of pregnant female rats from death and resorption. We will explore the hypothesis that vitamin E supplements containing a chemical distribution of tocopherols and tocotrienols similar to that found in plant oils may be superior to supplements containing only a-tocopherol or a-tocopheryl acetate. Finally, this review will summarize the very recent application of nutritional genomics to vitamin E synthesis in plants. 

Merder, C. and Chabardes, P. (1994) OrganometaDic chemistry in industrial vitamin A and vitamin E synthesis. Pure Appl. Chem., 66,1509-1518. 

Nanoscaled Metal (Hydroxide) Fluoride-Catalyzed Fine Chemical Synthesis (All-rac)-(x-tocopherol (vitamin E) synthesis 155... 

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