Synthesis of Vitamin E

Vitamins and Hormones

Volumn 76, Issue , 2007, Pages 155-202

  Netscher, Thomas ^a  

^a Research and Development   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT;

CHEMISTRY; CONFORMATION; REVIEW; SYNTHESIS;

ANTIOXIDANTS; MOLECULAR CONFORMATION; VITAMIN E;

EID: 34447099395     PISSN: 00836729     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0083-6729(07)76007-7     Document Type: Review

References (165)

1. Akutagawa S. Asymmetric synthesis by metal BINAP catalysts. Appl. Catal. A: General 128 (1995) 171-207
2. Asgill J.O., Crombie L., and Whiting D.A. Chromenylation of 2-naphthol and alkylhydroquinones: Short syntheses of (2RS,4′R,8′R)-α-tocopherol (vitamin E) and (2RS,4′R,8′R)-β-tocopherol. J. Chem. Soc., Chem. Commun. (1978) 59-60
3. Baldenius K.U., von dem Bussche-Hünnefeld L., Hilgemann E., Hoppe P., and Stürmer R. Vitamin E (tocopherols, tocotrienols). "Ullmann's Encyclopedia of Industrial Chemistry," and 594-597 Vol. A27 (1996), VCH Verlagsgesellschaft, Weinheim 478-488
4. Baldenius K.U., Bockstiegel B., Jaedicke H., Ruff D., Siedenbiedel C., and Stürmer R. Verfahren zur Herstellung von Chromanol-Derivaten (2000) EP 0 989 126 A1
5. 5-Synthon. Helv. Chim. Acta 62 (1979) 2384-2399
6. Bell S., Wüstenberg B., Kaiser S., Menges F., Netscher T., and Pfaltz A. Asymmetric hydrogenation of unfunctionalized, purely alkyl-substituted olefins. Science 311 (2006) 642-644
7. Bienayme H., Ancel J.-E., Meilland P., and Simonato J.-P. Rhodium(I)-catalyzed addition of phenols to dienes. A new convergent synthesis of vitamin E. Tetrahedron Lett. 41 (2000) 3339-3343
8. Bonrath W., and Netscher T. Catalytic processes in vitamins synthesis and production. Appl. Catal. A: General 280 (2005) 55-73
9. Bonrath W., and Schneider M. Manufacture of trimethylhydroquinone diacylates (2003) WO 2003/051812 A1
10. Bonrath W., Karge R., and Netscher T. Lipase-catalyzed transformations as key-steps in the large-scale preparation of vitamins. J. Mol. Catal. B: Enzym. 19-20 (2002) 67-72
11. Bonrath W., Eisenkrätzer D., Enjolras V., Karge R., Netscher T., and Schneider M. Process for the manufacture of a vitamin E intermediate (2002) EP 1 239 045 A1
12. Bonrath W., Haas A., Hoppmann E., Netscher T., Pauling H., Schager F., and Wildermann A. Synthesis of (all-rac)-α-tocopherol using fluorinated NH-acidic catalysts. Adv. Synth. Catal. 344 (2002) 37-39
13. Bonrath W., Dittel C., Pabst T., Netscher T., Schmid R., and Zwartjes I. Stereoselective O → C allylic rearrangement and ring-closure reaction: A novel route to tocopherols, XXXV. Jahrestreffen Deutscher Katalytiker, 20-22 March 2002, Weimar (Germany), Poster P 135 (2002) 312-313 book of abstracts
14. Bonrath W., Burdick D.C., Netscher T., Schager F., and Thomas D. Manufacture of (all-rac)-α-tocopherol via acid-catalyzed ring closure (2003) WO 2003/037883 A1
15. Bonrath W., Dittel C., Netscher T., Pabst T., and Schmid R. Manufacture of tocopheryl acetate (2004) WO 2004/046126 A1
16. Bonrath W., Menges F., Netscher T., Pfaltz A., and Wüstenberg B. Asymmetric hydrogenation of alkenes using chiral iridium complexes (2006) WO 2006/066863 A1
17. Bonrath W., Dittel C., Giraudi L., Netscher T., and Pabst T. Rare earth triflate catalysts in the synthesis of vitamin E and its derivatives. Catal. Today 121 (2007) 65-70
18. Breit B., and Demel P. Copper-mediated and -catalyzed o-DPPB-directed allylic substitution. Adv. Synth. Catal. 343 (2001) 429-432
19. Broger E.A., and Müller R.K. Verfahren zur Herstellung von Isoprenderivaten (1993) EP 0 565 975 A2
20. Chan K.-K., and Saucy G. Transfer of chirality in the [2,3] sigmatropic rearrangement of allylic alcohols to β,γ-unsaturated amides. Preparation of optically active nine- and fourteen-carbon saturated isoprenoid synthons. J. Org. Chem. 42 (1977) 3828-3832
21. Chan K.-K., Cohen N., De Noble J.P., Specian Jr. A.C., and Saucy G. Synthetic studies on (2R,4′R,8′R)-α-tocopherol. Facile syntheses of optically active, saturated, acyclic isoprenoids via stereospecific [3,3] sigmatropic rearrangements. J. Org. Chem. 41 (1976) 3497-3505
22. Chan K.-K., Specian Jr. A.C., and Saucy G. Synthesis of (2R,4′R,8′R)-α-tocopheryl acetate (vitamin E acetate) using [3,3] sigmatropic rearrangement. J. Org. Chem. 43 (1978) 3435-3440
23. Chauvel A., Delmon B., and Hölderich W.F. New catalytic processes developed in Europe during the 1980's. Appl. Catal. A: General 115 (1994) 173-217
24. Chen C.Y., Nagumo S., and Akita H. A synthesis of (2R,4′R,8′R)-α-tocopherol (vitamin E) side chain. Chem. Pharm. Bull. 44 (1996) 2153-2156
25. Chênevert R., and Courchesne G. Synthesis of (S)-α-tocotrienol via an enzymatic desymmetrization of an achiral chroman derivative. Tetrahedron Lett. 43 (2002) 7971-7973
26. Chênevert R., Courchesne G., and Pelchat N. Chemoenzymatic synthesis of both enantiomers of α-tocotrienol. Bioorg. Med. Chem. 14 (2006) 5389-5396
27. Coffen D.L., Cohen N., Pico A.M., Schmid R., Sebastian M.J., and Wong F. A microbial lipase based stereoselective synthesis of (d)-α-tocopherol from (R)-citronellal and (S)-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid. Heterocycles 39 (1994) 527-552
28. Cohen N., Eichel W.F., Lopresti R.J., Neukom C., and Saucy G. Synthetic studies on (2R,4′R,8′R)-α-tocopherol. An approach utilizing side chain synthons of microbiological origin. J. Org. Chem. 41 (1976) 3505-3511
29. Cohen N., Lopresti R.J., and Saucy G. A novel total synthesis of (2R,4′R,8′R)-α-tocopherol (vitamin E). Construction of chiral chromans from an optically active, nonaromatic precursor. J. Am. Chem. Soc. 101 (1979) 6710-6716
30. Cohen N., Lopresti R.J., and Neukom C. Studies on the total synthesis of (2R,4′R,8′R)-α-tocopherol (vitamin E). Stereospecific cyclizations leading to optically active chromans. J. Org. Chem. 46 (1981) 2445-2450
31. Cohen N., Scott C.G., Neukom C., Lopresti R.J., Weber G., and Saucy G. Total synthesis of all eight stereoisomers of α-tocopheryl acetate. Determination of their diastereoisomeric and enantiomeric purity by gas chromatography. Helv. Chim. Acta 64 (1981) 1158-1173
32. Cohen N., Banner B.L., and Neukom C. Improvements in the synthesis of a key α-tocopherol intermediate-(S)-(-)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benz opyran-2-acetic acid. Synth. Commun. 12 (1982) 57-65
33. Cohen N., Schaer B., and Scalone M. Synthesis of (2RS,4′R,8′R)-α-tocopherol and related compounds via a 2-chlorochroman. J. Org. Chem. 57 (1992) 5783-5785
34. Couladouros E.A., Papas A.M., Moutsos V.L., and Lampropoulou M. Process for synthesizing d-tocotrienols from 2-vinylchromane compound (2005) WO 2005/035491 A2; US 2005/0124688 A1
35. DellaPenna D., and Last R.L. Progress in the dissection and manipulation of plant vitamin E biosynthesis. Physiologica Plantarum 126 (2006) 356-368
36. DellaPenna D., and Pogson B.J. Vitamin synthesis in plants: Tocopherols and carotenoids. Annu. Rev. Plant Biol. 57 (2006) 711-738
37. Ernst H.G. Vitamin E (Tocopherole, Tocotrienole). "Ullmanns Encyclopädie der technischen Chemie," (1983), Verlag Chemie, Weinheim 643-649 Bd. 23, and 717-718
38. Ernst H., Gehrken H.-P., and Paust J. Verbessertes Verfahren zur Herstellung von α-Tocopherol (1984) DE 33 09 158 A1
39. Evans H.M., and Bishop K.S. On the existence of a hitherto unrecognized dietary factor essential for reproduction. Science 56 (1922) 650-651
40. Evans H.M., Emerson O.H., and Emerson G.A. The isolation from wheat germ oil of an alcohol, α-tocopherol, having the properties of vitamin E. J. Biol. Chem. 113 (1936) 319-332
41. Fernholz E. On the constitution of α-tocopherol. J. Am. Chem. Soc. 60 (1938) 700-705
42. Fujisawa T., Sato T., Kawara T., and Ohashi K. A stereocontrolled total synthesis of optically active (R,R)-phytol. Tetrahedron Lett. 22 (1981) 4823-4826
43. Goodhue C.T., and Schaeffer J.R. Preparation of L(+) β-hydroxyisobutyric acid by bacterial oxidation of isobutyric acid. Biotechnol. Bioeng. 13 (1971) 203-214
44. Gramatica P., Manitto P., Monti D., and Speranza G. New syntheses of optically active vitamin E side chain by chemoenzymatic approach. Tetrahedron 42 (1986) 6687-6692
45. Gramatica P., Manitto P., Monti D., and Speranza G. Stereoselective total synthesis of natural phytol via double bond reductions by baker's yeast. Tetrahedron 43 (1987) 4481-4486
46. Grütter C., Alonso E., Chougnet A., and Woggon W.-D. A biomimetic chromanol cyclization leading to α-tocopherol. Angew. Chem. Int. Ed. 45 (2006) 1126-1130
47. 3-α-tocotrienol as biological tracers of tocotrienols. J. Labelled Comp. Radiopharm. 49 (2006) 733-743
48. Gupta M.K. Processing to improve soybean oil quality. INFORM 4 no. 11 (1993) 1267-1272
49. Hasegawa A., Ishihara K., and Yamamoto H. Trimethylsilyl pentafluorophenylbis(trifluoromethanesulfonyl)methide as a super Lewis acid catalyst for the condensation of trimethylhydroquinone with isophytol. Angew. Chem. Int. Ed. 42 (2003) 5731-5733
50. Heiser B., Broger E.A., and Crameri Y. New efficient methods for the synthesis and in-situ preparation of ruthenium(II) complexes of atropisomeric diphosphines and their application in asymmetric catalytic hydrogenations. Tetrahedron: Asymmetry 2 (1991) 51-62
51. Hübscher J., and Barner R. Totalsynthese von natürlichem α-Tocopherol. 5. Mitteilung. Asymmetrische Alkylierung und asymmetrische Epoxidierung als Methoden zur Einführung der (R)-Konfiguration an C(2) des Chroman-Systems. Helv. Chim. Acta 73 (1990) 1068-1086
52. Hughes L., Slaby M., Burton G.W., and Ingold K.U. Syntheses of α- and γ-tocopherols selectively labelled with deuterium. J. Labelled. Comp. Radiopharm. 28 (1990) 1049-1057
53. Huo S., and Negishi E. A convenient and asymmetric protocol for the synthesis of natural products containing chiral alkyl chains via Zr-catalyzed asymmetric carboalumination of alkenes. Synthesis of phytol and vitamins E and K. Org. Lett. 3 (2001) 3253-3256
54. Hyatt J.A., and Skelton C. A kinetic resolution route to the (S)-chromanmethanol intermediate for synthesis of the natural tocols. Tetrahedron: Asymmetry 8 (1997) 523-526
55. Hyatt J.A., Kottas G.S., and Effler J. Development of synthetic routes to D,L- α-tocopherol (vitamin E) from biologically produced geranylgeraniol. Org. Process Res. Dev. 6 (2002) 782-787
56. Imfeld M. Verfahren zur Herstellung von Hydrochinonderivaten (1986) EP 0 183 042 A2
57. Inoue S., Ikeda H., Sato S., Horie K., Ota T., Miyamoto O., and Sato K. Improved general method of ortho-alkylation of phenols using alkyl isopropyl sulfide, sulfuryl chloride, and triethylamine. An expedient synthesis of representative oxygen heterocycles and (2R,4′R,8′R)-α-tocopherol. J. Org. Chem. 52 (1987) 5495-5497
58. Ishihara K., Kubota M., and Yamamoto H. Practical synthesis of (±)-α-tocopherol. Trifluoromethanesulfonimide as an extremely active Broensted acid catalyst for the condensation of trimethylhydroquinone with isophytol. Synlett (1996) 1045-1046
59. IUPAC-IUB. Nomenclature of tocopherols and related compounds. Eur. J. Biochem. 123 (1982) 473-475 Pure Appl. Chem., 54, 1507-1510
60. Kabbe H.J., and Heitzer H. Eine neue Synthese von 3,4-Dehydro-α-tocotrienol und Vitamin-E. Synthesis (1978) 888-889
61. Kajiwara M., Sakamoto O., and Ohta S. Studies on tocopherols II. Convenient synthesis of tocopherols. Heterocycles 14 (1980) 1995-1998
62. Kamal-Eldin A., and Åppelqvist L.-A. The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids 31 (1996) 671-701 Remark: This review provides an excellent overview, but it contains several errors of nomenclature and wrong structures drawn from literature. References with the correct nomenclature and the revised structures are also cited in that review
63. Karrer P., and Isler O. dl-Tocopherols and process for the manufacture of same (1946) US 2,411,967
64. Karrer P., and Isler O. Process for the preparation of synthetic dl-tocopherols (1946) US 2,411,968
65. Karrer P., and Rentschler H. Ein Tocol mit bicyclischer Seitenkette. Helv. Chim. Acta 27 (1944) 1297-1300
66. Karrer P., Fritzsche H., Ringier B.H., and Salomon H. α-Tocopherol. Helv. Chim. Acta 21 (1938) 520-525 Synthese des α-Tocopherols. Helv. Chim. Acta21, 820-825
67. Knierzinger A., and Scalone M. Verfahren zur Herstellung von Vinylverbindungen (1990) EP 0 392 389 A2
68. Knierzinger A., and Scalone M. Tocopherol synthesis: Chromane cyclization and catalysis (1992) US 5,110,955
69. Knierzinger A., Walther W., Weber B., Müller R.K., and Netscher T. Eine neue Methode zur stereochemischen Analyse offenkettiger terpenoider Carbonyl-Verbindungen. Helv. Chim. Acta 73 (1990) 1087-1107
70. Kokubo Y., Hasegawa A., Kuwata S., Ishihara K., Yamamoto H., and Ikariya T. Synthesis of (all-rac)-α-tocopherol in supercritical carbon dioxide: Tuning of the product selectivity in batch and continuous-flow reactors. Adv. Synth. Catal. 347 (2005) 220-224
71. Koreeda M., and Brown L. Chirality transfer in stereoselective synthesis. A highly stereoselective synthesis of optically active vitamin E side chain. J. Org. Chem. 48 (1983) 2122-2124
72. Laufer M.C., Bonrath W., and Hoelderich W.F. Synthesis of (all-rac)-α-tocopherol using Nafion resin/silica nanocomposite materials as catalysts. Catal. Lett. 100 (2005) 101-103
73. Leuenberger H.G.W., and Wirz B. Biotransformations leading to optically active synthons for the preparation of fine chemicals. Chimia 47 (1993) 82-85
74. Leuenberger H.G.W., Boguth W., Barner R., Schmid M., and Zell R. Herstellung bifunktioneller, optisch aktiver Synthesebausteine für die Seitenkette mit Hilfe mikrobiologischer Umwandlungen. Helv. Chim. Acta 62 (1979) 455-463
75. Malaisé G., Bonrath W., Breuninger M., and Netscher T. A new route to vitamin E key-intermediates by olefin cross-metathesis. Helv. Chim. Acta 89 (2006) 797-812
76. Matsui M. Synthesis of α-tocopherol for the next century. Nihon Yukagakkaishi. J. Jpn. Oil Chem. Soc. 45 (1996) 821-831 Chem. Abstr.125, 301241
77. Matsui M., and Yamamoto H. Direct construction of the chroman structure from 1,3-diene. Regioselective protonation of acyclic polyene. Bull. Chem. Soc. Jpn. 68 (1995) 2657-2661
78. Matsui M., Karibe N., Hayashi K., and Yamamoto H. Synthesis of α-tocopherol: Scandium(III) trifluoromethanesulfonate as an efficient catalyst in the reaction of hydroquinone with allylic alcohol. Bull. Chem. Soc. Jpn. 68 (1995) 3569-3571
79. Matsumoto A., Takahashi S., Nakano K., and Kijima S. Identification of a new form of vitamin E in plant oil. Yukagaku 44 (1995) 593-597 Chem. Abstr.123, 226445
80. Mayer H., and Isler O. Synthesis of vitamins E. Methods Enzymol. 18 (1971) 241-348
81. Mayer H., Schudel P., Rüegg R., and Isler O. Über eine neue Vitamin-E-Synthese. Chimia 16 (1962) 367-368
82. Mayer H., Schudel P., Rüegg R., and Isler O. Die Totalsynthese von (2R,4′R,8′R)- und (2S,4′R,8′R)-α-Tocopherol. Helv. Chim. Acta 46 (1963) 650-671
83. Mayer H., Schudel P., Rüegg R., and Isler O. Die absolute Konfiguration des natürlichen α-Tocopherols. Helv. Chim. Acta 46 (1963) 963-982
84. Mayer H., Vetter W., Metzger J., Rüegg R., and Isler O. Die stereospezifische Cyclisierung von (3′R,7′R,11′R)-α-Tocopherolchinon. Helv. Chim. Acta 50 (1967) 1168-1178
85. Mayer H., Metzger J., and Isler O. Die Stereochemie von natürlichem γ-Tocotrienol (Plastochromanol-3), Plastochromanol-8 und Plastochromenol-8. Helv. Chim. Acta 50 (1967) 1376-1393
86. 3)-(all-rac)- δ-tocopherol. Eur. J. Org. Chem. (2003) 2840-2844
87. 3)- α-CEHC, a labeled analogue of a major vitamin E metabolite. J. Org. Chem. 69 (2004) 9303-9306
88. Mazzini F., Netscher T., and Salvadori P. Easy route to labeled and unlabeled R,R,R-γ-tocopherol by aryl demethylation of α-homologues. Tetrahedron 61 (2005) 813-817
89. 3]-γ-CEHC. Eur. J. Org. Chem. (2006) 5588-5593
90. McHale D., Green J., Marcinkiewicz S., Feeney J., and Sutcliffe L.H. Tocopherols. Part VIII. Structural and synthetic studies of ε-tocopherol. J. Chem. Soc. (1963) 784-791
91. Mercier C., and Chabardes P. Organometallic chemistry in industrial vitamin A and vitamin E synthesis. Pure Appl. Chem. 66 (1994) 1509-1518
92. Mercier C., Mignani G., Aufrand M., and Allmang G. Efficient synthesis of pseodoionone by oxidative decarboxylation of allyl β-ketoesters. Tetrahedron Lett. 32 (1991) 1433-1436
93. Millis J.R., Saucy G.G., Maurina-Brunker J., McMullin T.W., and Hyatt J.A. Method of vitamin production (2000) WO 00/01649
94. Millis J.R., Saucy G.G., Maurina-Brunker J., and McMullin T.W. Method of vitamin production (2000) WO 00/01650
95. Millis J.R., Saucy G.G., Maurina-Brunker J., McMullin T.W., and Hyatt J.A. Method of vitamin production (2001) US 6,242,227 B1
96. Mimoun H. Catalytic opportunities in the flavor and fragrance industry. Chimia 50 (1996) 620-625
97. Mizuguchi E., and Achiwa K. Oxalate as an activated ester group in lipase-catalyzed enantioselective hydrolysis: A versatile approach to d-α-tocopherol. Tetrahedron: Asymmetry 4 (1993) 2303-2306 Remark: The designations "enantioselectivity" and "enantiomeric purity" have to be changed to "diastereoselectivity" and "diastereoisomeric purity", as well as "ee" (enantiomeric excess) has to be replaced by "de" (diasteroisomeric excess), due to the presence of additional two chiral centers in the side chain of both starting materials and products
98. Mizuguchi E., and Achiwa K. Asymmetric synthesis of (S)-chromanmethanol as a useful synthetic unit of vitamin E analogs. Synlett (1995) 1255-1256
99. Mizuguchi E., Suzuki T., and Achiwa K. Lipase-catalyzed synthesis of optically active N,N,N-triethylethanaminium α-tocopherol analog MDL-73404. Synlett (1994) 929-930
100. Netscher T. Stereoisomers of tocopherols-syntheses and analytics. Chimia 50 (1996) 563-567
101. Netscher T. Synthesis and production of vitamin E. In: Gunstone F.D. (Ed). "Lipid Synthesis and Manufacture" (1999), Sheffield Academic Press Ltd., Sheffield, UK 250-267
102. Netscher T. Sulfonate leaving groups for nucleophilic substitution reactions-improved structures and procedures. Recent Res. Dev. Org. Chem. 7 (2003) 71-83
103. Netscher T. Preparation of trialkyl-substituted olefins by ruthenium catalyzed cross-metathesis. J. Organomet. Chem. 691 (2006) 5155-5162
104. Netscher T., and Bohrer P. Nucleophilic substitution reaction at the (oxo-) neopentylic center in the synthesis of tocopherols and analogues. Chimia 47 (1993) 295 Fall Meeting of the New Swiss Chemical Society, 22 October 1993, Basel, Switzerland, Abstract Organische Chemie, Poster
105. Netscher T., and Gautschi I. Präparative Enantiomerentrennung einer Chroman-2-Carbonsäure durch Chromatographie von Glucose-Derivaten. Liebigs Ann. Chem. (1992) 543-546
106. Netscher T., Scalone M., and Schmid R. Enantioselective hydrogenation: Towards a large-scale total synthesis of (R,R,R)-α-tocopherol. In: Blaser H.-U., and Schmidt E. (Eds). "Asymmetric Catalysis on Industrial Scale" (2004), Wiley-VCH, Weinheim, Germany 71-89
107. Netscher T., Müller R.K., Schneider J., Schneider H., Bohrer P., and Jestin R. Aminomethylation of vitamin E compounds. In: Seijas J.A. (Ed). "International Electronic Conferences on Synthetic Organic Chemistry, 5th, 6th, Sept. 1-30, 2001 and 2002, and 7th, 8th, Nov. 1-30, 2003 and 2004" (2004), Molecular Diversity Preservation International, Basel, Switzerland. http://www.mdpi.net/ecsoc/ecsoc-5/Papers/c0007/c0007.htm
108. Netscher T., Malaisé G., Bonrath W., and Breuninger M. Olefin cross-metathesis in natural product synthesis: Preparation of trisubstituted olefins on the way to vitamin E. Actual. Chim. 293 (2006) 21-23
109. Netscher T., Mazzini F., and Jestin R. Tocopherols by hydride reduction of dialkylamino derivatives. Eur. J. Org. Chem. (2007) 1176-1183
110. Noyori R., and Takaya H. BINAP: An efficient chiral element for asymmetric catalysis. Acc. Chem. Res. 23 (1990) 345-350
111. Oda S., Sugai T., and Ohta H. Synthesis of optically active citronellol, citronellal, and citronellic acid by microbial oxidation and double coupling system in an interface bioreactor. Bull. Chem. Soc. Jpn. 73 (2000) 2819-2823
112. 1-chromanol, and their analogs in the presence of aluminosilicate catalysts Tseokar-10 and Pentasil. ARKIVOC 13 (2003) 101-118
113. Outten R.A., Bohrer P., Müller R.K., Schneider H., Rüttimann A., and Netscher T. Routes to vitamin E: Palladium-mediated arylation of optically active acetylene and ethylene building blocks. Chem. Listy. Symposia 93 (1999) S49 presented by T.N. at 18th Conference on Isoprenoids; 10-16 September 1999, Prachatice, Czech Republic
114. Outten R.A., Bohrer P., Müller R.K., Schneider H., Rüttimann A., and Netscher T. Palladium-catalyzed coupling reactions: Key-steps in stereoselective syntheses of tocopherols (1999) presented by T.N. at 11th European Symposium on Organic Chemistry, Göteborg, Sweden, July 23-28, 1999, Poster
115. Pearce B.C., Parker R.A., Deason M.E., Qureshi A.A., and Kim Wright J.J. Hypocholesterolemic activity of synthetic and natural tocotrienols. J. Med. Chem. 35 (1992) 3595-3606
116. Pearce B.C., Parker R.A., Deason M.E., Dischino D.D., Gillespie E., Qureshi A.A., Volk K., and Kim Wright J.J. Inhibitors of cholesterol biosynthesis. 2. Hypocholesterolemic and antioxidant activities of benzopyran and tetrahydronaphthalene analogues of the tocotrienols. J. Med. Chem. 37 (1994) 526-541
117. Pongracz G., Weiser H., and Matzinger D. Tocopherole-Antioxidantien der Natur. Fat Sci. Technol. 97 (1995) 90-104
118. Rein C., and Breit B. Total synthesis of (2R,4′R,8′R′)-α-tocopherol. 9th International SFB Symposium, (2005), Aachen, Germany P184
119. Riegl J., Brüggemann K., and Netscher T. Efficient preparation of (2R,4′R,8′R)-α-tocopherol by hydroxymethylation. In: Pombo-Villar E. (Ed). "Proceedings of ECSOC-3, and Proceedings of ECSOC-4, Sept. 1-30, 1999 and 2000" (2000), Molecular Diversity Preservation International, Basel, Switzerland. http://pages.unibas.ch/mdpi/ecsoc-4/c0035/c0035.htm
120. Sato K., Miyamoto O., Inoue S., and Sato S. Preparation of d-α-tocotrienol from geranylgeraniol. JP 63-63674;. Chem. Abstr. 110 (1988) 193145
121. Sato K., Inoue S., and Murayama T. Preparation of optically active α-tocotrienol. JP 1-233278;. Chem. Abstr. 112 (1989) 139621
122. Saucy G., and Cohen N. Asymmetric reactions applied to the synthesis of d-α-tocopherol. In: Yoshida Z. (Ed). "New Synthetic Methodology and Biologically Active Substances" (1981), Elsevier, Amsterdam 155-175
123. Schiefer G., Müller R.K., Schneider H., Umiker M., and Netscher T. Dehydrotocopherols-new vitamin E components. Chimia 53 (1999) 359 Fall Meeting of the New Swiss Chemical Society, 12 October 1999, Basel, Switzerland, Abstract Organic Chemistry 135
124. Schmid R., and Broger E.A. Asymmetric hydrogenation in process research of pharmaceuticals, vitamins and fine chemicals. Proceedings of the Chiral Europe '94 Symposium 19-20 Sept. 1994, Nice, France (1994) 79-86
125. Schmid R., Cereghetti M., Heiser B., Schönholzer P., and Hansen H.J. Axially dissymmetric bis(triaryl)phosphines in the biphenyl series: Synthesis of (6,6′-dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and analogues, and their use in rhodium(I)-catalyzed asymmetric isomerizations of N,N-diethylnerylamine. Helv. Chim. Acta 71 (1988) 897-929
126. Schmid R., Foricher J., Cereghetti M., and Schönholzer P. Axially dissymmetric diphosphines in the biphenyl series: Synthesis of (6,6′-dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine) ('MeOBIPHEP') and analogues via an ortho-lithiation/iodination Ullmann-reaction approach. Helv. Chim. Acta 74 (1991) 370-389
127. Schmid R., Broger E.A., Cereghetti M., Crameri Y., Foricher J., Lalonde M., Müller R.K., Scalone M., Schoettel G., and Zutter U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 68 (1996) 131-138
128. Schneider M., Zimmermann K., Aquino F., and Bonrath W. Industrial application of Nafion-systems in rearrangement-aromatisation, transesterification, alkylation, and ring-closure reactions. Appl. Catal. A: General 220 (2001) 51-58
129. Schudel P., Mayer H., Metzger J., Rüegg R., and Isler O. Die Umkehrung der Konfiguration am Kohlenstoffatom 2 von natürlichem (2R,4′R,8′R)-α-Tocopherol. Helv. Chim. Acta 46 (1963) 333-343
130. 1- und ε-Tocopherol. Helv. Chim. Acta 46 (1963) 2517-2526
131. Schudel P., Mayer H., and Isler O. 16. Tocopherols, II. Chemistry. In: Sebrell W.H., and Harris R.S. (Eds). "The Vitamins" Vol. V (1972), Academic Press, New York 168-218
132. Scott J.W., Bizzarro F.T., Parrish D.R., and Saucy G. Syntheses of (2R,4′R,8′R)-α-tocopherol and (2R,3′E,7′E)-α-tocotrienol. Helv. Chim. Acta 59 (1976) 290-306
133. Shchegolev A.A., Sarycheva I.K., Kochetova E.V., Mosolova O.V., Kulish M.A., and Evstigneeva R.P. Synthesis of vitamin E acetate. Khimiko-farmatsevticheskii Zhurnal 17 (1983) 92-95 Chem. Abstr.98 160971
134. Solladie G., and Moine G. Application of chiral sulfoxides in asymmetric synthesis: The enantiospecific synthesis of the chroman ring of α-tocopherol (vitamin E). J. Am. Chem. Soc. 106 (1984) 6097-6098
135. Stocker A., Rüttimann A., and Woggon W.-D. Identification of tocopherol-cyclase in the blue-green algae Anabaena variabilis Kützing (cyanobacteria). Helv. Chim. Acta 76 (1993) 1729-1738
136. Stocker A., Netscher T., Rüttimann A., Müller R.K., Schneider H., Todaro L.J., Derungs G., and Woggon W.-D. The reaction mechanism of chromanol-ring formation catalyzed by tocopherol cyclase from Anabaena variabilis Kützing (cyanobacteria). Helv. Chim. Acta 77 (1994) 1721-1737
137. Stocker A., Fretz H., Frick H., Rüttimann A., and Woggon W.-D. The substrate specificity of tocopherol cyclase. Bioorg. Med. Chem. 4 (1996) 1129-1134
138. Sugai T., Watanabe N., and Ohta H. A synthesis of natural α-tocopherol intermediate. Tetrahedron: Asymmetry 2 (1991) 371-376
139. Takabe K., Okisaka K., Uchiyama Y., Katagiri T., and Yoda H. An efficient synthesis of (S)-chromanmethanol, a vitamin E precursor. Chem. Lett. (1985) 561-562
140. Takano S., Sugihara T., and Ogasawara K. An efficient stereoselective preparation of vitamin E (α-tocopherol) from phytol. Synlett (1990) 451-452
141. Takano S., Yoshimizu T., and Ogasawara K. Use of the Sharpless asymmetric dihydroxylation as a substitute for the Katsuki-Sharpless asymmetric epoxidation: An alternative route to vitamin E and prostaglandin intermediates. Synlett (1994) 119-120
142. Takaya H., Ohta T., Sayo N., Kumobayashi H., Akutagawa S., Inoue S., Kasahara I., and Noyori R. Enantioselective hydrogenation of allylic and homoallylic alcohols. J. Am. Chem. Soc. 109 (1987) 1596-1597
143. Tani K., Yamagata T., Akutagawa S., Kumobayashi H., Taketomi T., Takaya H., Miyashita A., Noyori R., and Otsuka S. Metal-assisted terpenoid synthesis. 7. Highly enantioselective isomerization of prochiral allylamines catalyzed by chiral diphosphine rhodium(I) complexes. Preparation of optically active enamines. J. Am. Chem. Soc. 106 (1984) 5208-5217
144. Tietze L.F., and Görlitzer J. Preparation of chiral building blocks for a highly convergent vitamin E synthesis. Systematic investigations on the enantioselectivity of the Sharpless bishydroxylation. Synthesis (1998) 873-878
145. Tietze L.F., Görlitzer J., Schuffenhauer A., and Hübner M. Enantioselective synthesis of the chroman moiety of vitamin E. Eur. J. Org. Chem. (1999) 1075-1084
146. Tietze L.F., Peters H.J., Djalali Bazzaz F., and Seibel J. Katalytische Antikörper und ein Verfahren zur Herstellung von Chromanen über Zyklisierung mit diesen Antikörpern (2000) DE 198 52 903 A1
147. Tietze L.F., Sommer K.M., Zinngrebe J., and Stecker F. Palladium-catalyzed enantioselective domino reaction for the efficient synthesis of vitamin E. Angew. Chem. Int. Ed. 44 (2005) 257-259
148. Tietze L.F., Stecker F., Zinngrebe J., and Sommer K.M. Enantioselective palladium-catalyzed total synthesis of vitamin E by employing a domino Wacker-Heck reaction. Chem. Eur. J. 12 (2006) 8770-8776
149. Trost B.M. Asymmetric allylic alkylation, an enabling methodology. J. Org. Chem. 69 (2004) 5813-5837
150. Trost B.M., and Asakawa N. An asymmetric synthesis of the vitamin E core by Pd catalyzed discrimination of enantiotopic alkene faces. Synthesis (1999) 1491-1494
151. Trost B.M., and Toste F.D. A catalytic enantioselective approach to chromans and chromanols. A total synthesis of (-)-calanolides A and B and the vitamin E nucleus. J. Am. Chem. Soc. 120 (1998) 9074-9075
152. Trost B.M., Shen H.C., Dong L., Surivet J.-P., and Sylvain C. Synthesis of chiral chromans by Pd-catalyzed asymmetric allylic alkylation (AAA): Scope, mechanism, and applications. J. Am. Chem. Soc. 126 (2004) 11966-11983
153. Urano S., Nakano S.-I., and Matsuo M. Synthesis of dl-α-tocopherol and dl-α-tocotrienol. Chem. Pharm. Bull. 31 (1983) 4341-4345
154. Vecchi M., Walther W., Glinz E., Netscher T., Schmid R., Lalonde M., and Vetter W. Chromatographische Trennung und quantitative Bestimmung aller acht Stereoisomeren von α-Tocopherol. Helv. Chim. Acta 73 (1990) 782-789
155. Walsh L., Winters R.L., and Gonzalez R.G. Optimizing deodorizer distillate tocopherol yields. INFORM 9 no. 1 (1998) 78-83
156. Walther W., and Netscher T. Design and development of chiral reagents for the chromatographic e.e. determination of chiral alcohols. Chirality 8 (1996) 397-401
157. TM methyl ether: A powerful derivatizing reagent for the GC determination of the enantiomers of aliphatic alcohols. Chimia 45 (1991) 121-123
158. Weimann B.J., and Weiser H. Function of vitamin E in reproduction and in prostacyclin and immunoglobulin synthesis in rats. Am. J. Clin. Nutr. 53 (1991) 1056S-1060S
159. Weiser H., and Vecchi M. Stereoisomers of α-tocopheryl acetate. II. Biopotencies of all eight stereoisomers, individually or in mixtures, as determined by rat resorption-gestation tests. Internat. J. Vit. Nutr. Res. 52 (1982) 351-370
160. Wildermann A., Foricher Y., Netscher T., and Bonrath W. New application of indium catalysts: A novel and green concept in fine chemical industry. Pure Appl. Chem. (2007) in press
161. Wirz B., Schmid R., and Walther W. Enzymatic preparation of (R)-3-hydroxy-2-methylpropyl butyrate by asymmetric hydrolysis. Biocatalysis 3 (1990) 159-167
162. Wirz B., Barner R., and Hübscher J. Facile chemoenzymatic preparation of enantiomerically pure 2-methylglycerol derivatives as versatile trifunctional C4-synthons. J. Org. Chem. 58 (1993) 3980-3984
163. Wüstenberg B. Iridium-katalysierte enantioselektive Hydrierung: Neue Substrate und Anwendungen (2003), University of Basel, Switzerland Ph.D Thesis
164. Yoda H., and Takabe K. Novel synthesis of (S)-(-)-chroman-2-carboxylic acid, a vitamin E precursor. Chem. Lett. (1989) 465-466
165. Young F.V.K., Poot C., Biernoth E., Krog N., O'Neill L.A., and Davidson N.G.J. Processing of fats and oils. In: Gunstone F.D., Harwood J.L., and Padley F.B. (Eds). "The Lipid Handbook" (1986), Chapman and Hall, London 181-247