Development of Agriculture Left-Overs: Fine Organic Chemicals from Wheat Hemicellulose-Derived Pentoses

  • Frédéric Martel
  • Boris Estrine
  • Richard Plantier-Royon
  • Norbert Hoffmann
  • Charles Portella
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 294)

Abstract

This review is dedicated to wheat hemicelluloses and its main components d-xylose and l-arabinose as raw materials for fine organic chemistry. The context of the wheat agro-industry, its by-products, and extraction and hydrolysis of hemicelluloses to produce the pentoses are considered. The straightforward preparation of pentose-based surfactants, their properties, and their situation in the field of carbohydrate-based surfactants are addressed. Multistep transformations of pentoses are also described, first from a methodology point of view, with the aim of producing multifunctional enantiopure building-blocks, then considering targeted natural and/or bioactive products. Selected reactions of furfural, an important dehydration product of pentoses, are also presented.

Keywords

d-Xylose Enantiopure building-blocks Furfural l-Arabinose Surfactants 

Abbreviations

δO/W

Oil/water interfacial tension

APG

Alkyl polyglucosides

APP

Alkyl polypentosides

CMC

Critical micelle concentration

DP

Degree of polymerization

d-Xyl

d-Xylose

GAG

Glycosaminoglycan

HLB

Hydrophilic–lipophilic balance

l-Ara

l-Arabinose

MOE

Modulus of elasticity

MOR

Modulus of rupture

MTHF

Methyltetrahydrofuran

RCM

Ring-closing metathesis

GAG

Glycosaminoglycan

References

  1. 1.
    Allen E, Vocke G (2006) Wheat situation and outlook yearbook. In: Knauth C (ed) USDA WHS-2006 publicationsGoogle Scholar
  2. 2.
    Klass DL (2004) Biomass for renewable energy and fuels. In: Encyclopedia of energy, Elsevier Inc.Google Scholar
  3. 3.
    Theander O, Westerlund E, Aman P (1993) Cereal Food World 33:135–141Google Scholar
  4. 4.
    Brillouet JM, Joseleau JP (1987) Carbohydr Res 159:109–126CrossRefGoogle Scholar
  5. 5.
    Sun R, Mark Lawther J, Banks WB (1996) Carbohydr Polymer 29:325–331CrossRefGoogle Scholar
  6. 6.
    Torget R, Hatzis C, Hayward TK, Hsu TA, Philippidis GP (1996) Appl Biochem Biotechnol 57/58:85–101CrossRefGoogle Scholar
  7. 7.
    Bataillon M, Mathaly P, Nunes Cardinali AP, Duchiron F (1998) Ind Crop Prod 8:37–43CrossRefGoogle Scholar
  8. 8.
    Maes C, Delcour A (2001) J Cereal Sci 34:29–35CrossRefGoogle Scholar
  9. 9.
    Lequart C, Nuzillard JM, Kurek B, Debeire P (1999) Carbohydr Res 319:102–111CrossRefGoogle Scholar
  10. 10.
    Ternrud IE, Lindberg JE, Magnusson AT, Theander O (1988) J Sci Food Agric 42:9–18CrossRefGoogle Scholar
  11. 11.
    San Miguel Bento L (1990) Int Sugar J 92:116–125Google Scholar
  12. 12.
    Schenk FW (1992) Refining: carbon treatment and reactive precoats. In: Schenk W (ed) Starch hydrolysis products. VCH, USAGoogle Scholar
  13. 13.
    Focus on surfactants (2008) Special Chem Mag 6:5Google Scholar
  14. 14.
    Hirsinger F (1997) Life-cycle inventory. In: Rybinski W, Hill K (eds) Alkyl polyglycosides: technology properties and applications. Wiley-VCH, WeinheimGoogle Scholar
  15. 15.
    Biermann M, Schmid K, Shulz P (1994) Alkyl polyglycosides: technology and properties. Henkel Referate 30:7–15Google Scholar
  16. 16.
    Rybinski W, Hill K (1998) Angew Chem Int Ed 37:1328–1345CrossRefGoogle Scholar
  17. 17.
    Van der Burgh LF, Sommer SJ (1983) Eur Patent EP 92355Google Scholar
  18. 18.
    Lüders H (1987) Technical processes for manufacturing alkyl polyglucosides. In: Balzer D, Harald L (eds) Nonionic surfactants – alkyl polyglucosides. Marcel Dekker, New York and BaselGoogle Scholar
  19. 19.
    Lüders H (1987) Eur Patent EP 253996Google Scholar
  20. 20.
    Eskuchen R, Nitsche M (1997) Technology and production of alkyl polyglycosides. In: Rybinski W, Hill K (eds) Alkyl polyglycosides: technology properties and applications. Wiley-VCH, WeinheimGoogle Scholar
  21. 21.
  22. 22.
    Kamm B, Kamm M, Schmidt M, Hirth T, Schulze M (2006) Biorefineries – industrial processes and products. In: Kamm B, Gruber PR, Kamm M (eds) Biorefineries industrial processes and products. Wiley-VCH, WeinheimGoogle Scholar
  23. 23.
    Bertho JN, Mathaly P, Dubois V, De Baynast R (1997) US 5688930Google Scholar
  24. 24.
    Augé J (2008) Green Chem 10:225–231CrossRefGoogle Scholar
  25. 25.
    Wust W, Eskuchen R (1990) EP 0357969Google Scholar
  26. 26.
    Augé J, Sizun G (2009) Green Chem 11:1179–1183CrossRefGoogle Scholar
  27. 27.
    Estrine B, Bouquillon S, Hénin F, Muzart J (2004) Eur J Org Chem 2914–2922Google Scholar
  28. 28.
    Estrine B, Bouquillon S, Hénin F, Muzart J (2005) Green Chem 7:219–223CrossRefGoogle Scholar
  29. 29.
    Estrine B, Bouquillon S, Hénin F, Muzart J (2003) WO 03 053987. Chem Abstr 139:54601Google Scholar
  30. 30.
    Hadad C, Damez C, Bouquillon S, Estrine B, Hénin F, Muzart J, Pezron I, Komunjer L (2006) Carbohydr Res 341:1938–1944CrossRefGoogle Scholar
  31. 31.
    Böcker T, Thiem J (1989) Tenside Surf Det 26:318–324Google Scholar
  32. 32.
    Ernenwein C, Estrine B (2004) FR 2869242Google Scholar
  33. 33.
    Estrine B, Ernenwein C, Marinkovic S (2008) FR 2913896Google Scholar
  34. 34.
    Estrine B, Ernenwein C, Brésin A, Wintrebert A, Benvegnu T, Plusquellec D (2004) FR 2869912Google Scholar
  35. 35.
    Estrine B (2005) Development of new environmentally friendly surfactants derived from wheat byproducts. First international conference on renewable resources and biorefineries, Ghent, BelgiumGoogle Scholar
  36. 36.
    Estrine B, (2008) Valorization of pentoses from biomass. Seventh World Surfactant Congress, Paris, FranceGoogle Scholar
  37. 37.
    Werpy T, Petersen G, Aden A, Bozel J, Holladay J, White J, Manheim A, Elliot D, Lasure L, Jones S, Gerber M, Ibsen K, Lumberg L, Kelley S (2004) Top value added chemicals from biomass. In: Results of screening for potential candidates from sugars and synthesis gas, vol 1. US Department of Energy. http://www1.eere.energy.gov/biomass/pdfs/35523.pdf
  38. 38.
    Granström TB, Izumori K, Leisola M (2007) Appl Microbiol Biotechnol 74:273–276CrossRefGoogle Scholar
  39. 39.
    Gosselin G, Bergogne M-C, Imbach J-L (1991) Nucleic Acid Chem 4:41–45Google Scholar
  40. 40.
    Gelas J, Horton D (1975) Carbohydr Res 45:181–195CrossRefGoogle Scholar
  41. 41.
    Okabe M, Sun RC, Zenchoff GB (1991) J Org Chem 56:4392–4397CrossRefGoogle Scholar
  42. 42.
    Sun RC, Okabe M (1995) Org Synth Coll 72:48–52Google Scholar
  43. 43.
    Gao J, Zhen ZB, Jian YJ, Wu Y (2008) Tetrahedron 64:9377–9383CrossRefGoogle Scholar
  44. 44.
    Zhen ZB, Gao J, Wu Y (2009) Chin J Chem 27:205–208CrossRefGoogle Scholar
  45. 45.
    Kireev AS, Breithaupt AT, Collins W, Nadein ON, Kornienko A (2004) J Org Chem 70:742–745CrossRefGoogle Scholar
  46. 46.
    Luchetti G, Ding K, d’Alarcao M, Kornienko A (2008) Synthesis 3142–3147Google Scholar
  47. 47.
    Ferrier RJ, Middleton S (1993) Chem Rev 93:2779–2831CrossRefGoogle Scholar
  48. 48.
    Martinez-Grau A, Marco-Contelles J (1998) Chem Soc Rev 27:155–162CrossRefGoogle Scholar
  49. 49.
    Dalko PI, Sinaÿ P (1999) Angew Chem Int Ed 38:773–777CrossRefGoogle Scholar
  50. 50.
    Madsen R (2007) Eur J Org Chem 399–415Google Scholar
  51. 51.
    Bernet B, Vasella A (1979) Helv Chim Acta 62:1990–2016CrossRefGoogle Scholar
  52. 52.
    Bernet B, Vasella A (1979) Helv Chim Acta 62:2400–2410CrossRefGoogle Scholar
  53. 53.
    Bernet B, Vasella A (1979) Helv Chim Acta 62:2411–2431CrossRefGoogle Scholar
  54. 54.
    Hyldtoft L, Poulsen CS, Madsen R (1999) Chem Commun 2101–2102Google Scholar
  55. 55.
    Hyldtoft L, Madsen R (2000) J Am Chem Soc 122:8444–8452CrossRefGoogle Scholar
  56. 56.
    Hansen FG, Bungaard E, Madsen R (2005) J Org Chem 70:10139–10142CrossRefGoogle Scholar
  57. 57.
    Poulsen CS, Madsen R (2002) J Org Chem 67:4441–4449CrossRefGoogle Scholar
  58. 58.
    Håkansson AE, Palmelund A, Holm H, Madsen R (2006) Chem Eur J 12:3243–3253CrossRefGoogle Scholar
  59. 59.
    Bercier A, Plantier-Royon R, Portella C (2007) Carbohydr Res 342:2450–2455CrossRefGoogle Scholar
  60. 60.
    Génu-Dellac C, Gosselin G, Imbach J-L (1991) Carbohydr Res 216:249–255CrossRefGoogle Scholar
  61. 61.
    Hénon E, Bercier A, Plantier-Royon R, Harakat D, Portella C (2007) J Org Chem 72:2271–2278CrossRefGoogle Scholar
  62. 62.
    Bercier A, Plantier-Royon R, Portella C (2010) to be publishedGoogle Scholar
  63. 63.
    Kim E, Gordon DM, Walther Schmid W, Whitesides GM (1993) J Org Chem 58:5500–5507CrossRefGoogle Scholar
  64. 64.
    Palmelund A, Madsen R (2005) J Org Chem 70:8248–8251CrossRefGoogle Scholar
  65. 65.
    Hadad C, Majoral JP, Muzart J, Caminade AM, Bouquillon S (2009) Tetrahedron 50:1902–1905CrossRefGoogle Scholar
  66. 66.
    Park S, Shin I (2007) Org Lett 9:1675–1678CrossRefGoogle Scholar
  67. 67.
    Camponovo J, Hadad C, Ruiz J, Cloutet E, Gatard S, Muzart J, Bouquillon S, Astruc D (2009) J Org Chem 74:5071–5074CrossRefGoogle Scholar
  68. 68.
    Barberousse V, Boubia B, Samreth S (2001) WO Patent 2001036437, Chem Abstr 134:353473Google Scholar
  69. 69.
    Mignon L, Goichot C, Ratel P, Cagnin G, Baudry M, Praly J-P, Boubia B, Barberousse V (2003) Carbohydr Res 338:1271–1282CrossRefGoogle Scholar
  70. 70.
    Barberousse V, Bondoux M, Thomas D, Peyrou V (2006) WO patent 2006100413. Chem Abstr 145:377529Google Scholar
  71. 71.
    Thomas D, Bondoux M, Barberousse V, Peyrou V (2008) WO patent 2008007027. Chem Abstr 148:144970Google Scholar
  72. 72.
    Bellamy F, Horton D, Millet J, Picart F, Samreth S, Chazan JB (1993) J Med Chem 36:898–903CrossRefGoogle Scholar
  73. 73.
    Bellamy F, Barberousse V, Martin N, Masson P, Millet J, Samreth S, Sepulchre C, Theveniaux J, Horton D (1995) Eur J Med Chem 30:101s–115sGoogle Scholar
  74. 74.
    Dubb JW, Henderson LS, Okada SS, Peyrou V, Samuels RE, Sheth S, Spera PA, Toomey JR, Wilson D (2006) WO patent 2006060647. Chem Abstr 145:1040Google Scholar
  75. 75.
    Barberousse V, Samreth S, Boubia B, Bellamy F, Peyrou V (2005) FR patent 2860234. Chem Abstr 142:336586Google Scholar
  76. 76.
    Bondoux M, Mignon L, Ou K, Renaut P, Thomas D, Barberousse V (2009) Tetrahedron Lett 50:3872–3876CrossRefGoogle Scholar
  77. 77.
    Dalko M, Breton L (2002) WO patent 2002051828. Chem Abstr 137:79179Google Scholar
  78. 78.
    Cassin G, Simmonet JT (2007) WO patent 2007020536. Chem Abstr 146:258259Google Scholar
  79. 79.
    Cavezza A, Boulle C, Guéguiniat A, Pichaud P, Trouille S, Ricard L, Dalko-Csiba M (2009) Bioorg Med Chem Lett 19:845–849CrossRefGoogle Scholar
  80. 80.
    Mani K, Havsmark B, Persson S, Kaneda Y, Yamamoto H, Sakurai K, Ashikari S, Habuchi H, Suzuki S, Kimata K, Malström A, Westergren-Thorsson G, Fransson LA (1998) Cancer Res 58:1099–1104Google Scholar
  81. 81.
    Mani K, Belting M, Ellervik U, Falk N, Svensson G, Sandgren S, Fransson LA (2004) Glycobiology 5:387–397CrossRefGoogle Scholar
  82. 82.
    Jacobsson M, Malmberg J, Ellervik U (2006) Carbohydr Res 341:1266–1281CrossRefGoogle Scholar
  83. 83.
    Johnsson R, Mani K, Ellervik U (2007) Bioorg Med Chem Lett 17:2338–2341CrossRefGoogle Scholar
  84. 84.
    Jacobsson M, Ellervik U (2002) Tetrahedron Lett 43:6549–6552CrossRefGoogle Scholar
  85. 85.
    Jacobsson M, Ellervik U, Belting M, Mani K (2006) J Med Chem 49:1932–1938CrossRefGoogle Scholar
  86. 86.
    Johnsson R, Mani K, Ellervik U (2007) Bioorg Med Chem 15:2868–2877CrossRefGoogle Scholar
  87. 87.
    Jacobsson M, Mani K, Ellervik U (2007) Bioorg Med Chem 15:5283–5299CrossRefGoogle Scholar
  88. 88.
    Keinicke L, Madsen R (2005) Org Biomol Chem 3:4124–4128CrossRefGoogle Scholar
  89. 89.
    Lucchetti G, Ding K, Kornienko A, d’Alarcao M (2008) Synthesis 3148–3154Google Scholar
  90. 90.
    Stütz AE (1999) Iminosugars as glycosidase inhibitors: nojirimycin and beyond. Wiley-VCH, Weinheim, Germany. ISBN 978-3-527-29544-9Google Scholar
  91. 91.
    Compain P, Martin OR (2007) Iminosugars, from synthesis to therapeutic applications. Wiley, Chichester. ISBN 978-0-470-03391-3CrossRefGoogle Scholar
  92. 92.
    Tsou E-L, Yeh Y-T, Liang P-H, Cheng W-C (2009) Tetrahedron 65:93–100CrossRefGoogle Scholar
  93. 93.
    Laroche C, Plantier-Royon R, Szymoniak J, Bertus P, Behr J-B (2006) Synlett 223–226Google Scholar
  94. 94.
    Laroche C, Behr J-B, Szymoniak J, Bertus P, Schütz C, Vogel P, Plantier-Royon R (2006) Bioorg Med Chem 14:4047–4054CrossRefGoogle Scholar
  95. 95.
    Pearson MSM, Floquet N, Bello C, Vogel P, Plantier-Royon R, Szymoniak J, Bertus P, Behr J-B (2009) Bioorg Med Chem 17:8020–8026CrossRefGoogle Scholar
  96. 96.
    Pearson MSM, Plantier-Royon R, Szymoniak J, Bertus P, Behr J-B (2007) Synthesis 3589–3594Google Scholar
  97. 97.
    Yoshikawa M, Murakami T, Shimada H, Matsuda H, Yamahara J, Tanabe G, Muraoka O (1997) Tetrahedron Lett 38:8367–8370CrossRefGoogle Scholar
  98. 98.
    Yoshikawa M, Morikawa T, Matsuda H, Tanabe G, Muraoka O (2002) Bioorg Med Chem 10:1547–1554CrossRefGoogle Scholar
  99. 99.
    Ozaki S, Oe H, Kitamura S (2008) J Nat Prod 71:981–984CrossRefGoogle Scholar
  100. 100.
    Oe H, Ozaki S (2008) Biosci Biotechnol Biochem 72:1962–1964CrossRefGoogle Scholar
  101. 101.
    Mohan S, Pinto BM (2007) Carbohydr Res 342:1551–1580CrossRefGoogle Scholar
  102. 102.
    Muraoka O, Yoshikai K, Takahashi H, Minematsu T, Lu G, Tanabe G, Wang T, Matsuda H, Yoshikawa M (2006) Bioorg Med Chem 14:500–509CrossRefGoogle Scholar
  103. 103.
    Liu H, Pinto BM (2005) J Org Chem 70:753–755CrossRefGoogle Scholar
  104. 104.
    Nasi R, Sim L, Rose DR, Pinto BM (2007) Carbohydr Res 342:1888–1894CrossRefGoogle Scholar
  105. 105.
    Simons C (2001) Nucleoside mimetics: their chemistry and biological properties. Gordon and Breach Science, The Netherlands. ISBN 90-5699-324-0Google Scholar
  106. 106.
    Okano K (2009) Tetrahedron 65:1937–1949CrossRefGoogle Scholar
  107. 107.
    Du J, Choi Y, Lee K, Chun BK, Hong JH, Chu CK (1999) Nucleosides & Nucleotides 18:187–195CrossRefGoogle Scholar
  108. 108.
    Akagi M, Omae D, Tamura Y, Ueda T, Kumashiro T, Urata H (2002) Chem Pharm Bull 50:866–868CrossRefGoogle Scholar
  109. 109.
    Stewart AJ, Evans RM, Weymouth-Wilson AC, Cowley AR, Watkin DJ, Fleet GWJ (2002) Tetrahedron Asymmetry 13:2667–2672CrossRefGoogle Scholar
  110. 110.
    Zeitsch KJ (2000) The chemistry and technology of furfural and its many by-products. Elsevier, AmsterdamGoogle Scholar
  111. 111.
    Mamman AS, Lee J-M, Kim Y-C, Hwang T, Park N-J, Hwang YK, Chang J-S, Hwang J-S (2008) Biofuels Bioprod Bioref 2:438–454CrossRefGoogle Scholar
  112. 112.
    Joule JA, Mills K (2000) Heterocyclic chemistry, 4th edn. Blackwell Science, OxfordGoogle Scholar
  113. 113.
    Kamm B, Kamm M, Schmidt M, Hirth T, Schulze M (2006) Lignocellulose-based chemical products and product family trees. In: Kamm B, Gruber PR, Kamm M (eds) Biorefineries industrial processes and products. Wiley-VCH, WeinheimGoogle Scholar
  114. 114.
    Aycock DF (2007) Org Process Res Dev 11:156–159CrossRefGoogle Scholar
  115. 115.
    Lande S, Westin M, Schneider M (2008) Mol Cryst Liq Cryst 484:367–378CrossRefGoogle Scholar
  116. 116.
    Lichtenthaler FW (2002) Acc Chem Res 35:728–737CrossRefGoogle Scholar
  117. 117.
    Zhu J, Bienaymé H (eds) (2005) Multicomponent reactions. Wiley-VCH, WeinheimGoogle Scholar
  118. 118.
    Lee D, Sello JK, Schreiber SL (2000) Org Lett 2:709–712CrossRefGoogle Scholar
  119. 119.
    Burke MD, Schreiber SL (2004) Angew Chem Int Ed 43:46–58CrossRefGoogle Scholar
  120. 120.
    Burke MD, Berger EM, Schreiber SL (2003) Science 302:613–618CrossRefGoogle Scholar
  121. 121.
    Holder NL (1982) Chem Rev 82:287–332CrossRefGoogle Scholar
  122. 122.
    Gopinath R, Barkakaty B, Talukdar B, Patel BK (2003) J Org Chem 68:2944–2947CrossRefGoogle Scholar
  123. 123.
    Tian Q, Shi D, Sha Y (2008) Molecules 13:948–957CrossRefGoogle Scholar
  124. 124.
    Mannam S, Sekar G (2008) Tetrahedron Lett 49:1083–1086CrossRefGoogle Scholar
  125. 125.
    Achmatowicz O, Bukowski P, Szechner B, Zwierzchowska Z, Zamojski A (1971) Tetrahedron 27:1973–1996CrossRefGoogle Scholar
  126. 126.
    Harries JM, Li M, Scott JG, O’Doherty GA (2004) Approach to 5,6-dihydro-2H-pyran-2-one containing natural products. In: Harmata M (ed) Strategies and tactics in organic synthesis, vol. 5. Elsevier, LondonGoogle Scholar
  127. 127.
    Honda T (1997) Oxidative ring transformation of 2-furylcarbinols in natural products. In: Atta-ur-Rahman (ed) Studies in natural products chemistry, vol. 19. Elsevier Science BV, AmsterdamGoogle Scholar
  128. 128.
    Georgiadis MP, Albizati KF, Georgiadis YM (1992) Org Prep Proced Int 24:95–118CrossRefGoogle Scholar
  129. 129.
    Couladouros EA, Strongilos AT (2002) Angew Chem Int Ed 41:3677–3680CrossRefGoogle Scholar
  130. 130.
    Ciufolini MA, Hermann CYW, Dong Q, Shimizu T, Swaminathan S, Xi N (1998) Synlett 105–114Google Scholar
  131. 131.
    Esser P, Pohlmann B, Scharf H-D (1994) Angew Chem Int Ed Engl 33:2009–2023CrossRefGoogle Scholar
  132. 132.
    Schenck GO (1953) Liebigs Ann Chem 584:156–176CrossRefGoogle Scholar
  133. 133.
    Bolz G, Wiersdorff (1972) BASF DE 2111119 A1Google Scholar
  134. 134.
    Cottier L, Descotes G, Nigay H, Parron J-C, Grégoire V (1986) Bull Soc Chim Fr 844–850Google Scholar
  135. 135.
    Hoffmann N (2008) Chem Rev 108:1052–1103CrossRefGoogle Scholar
  136. 136.
    Oelgemöller M, Jung C, Mattay J (2007) Pure Appl Chem 79:1939–1947CrossRefGoogle Scholar
  137. 137.
    Albini A, Fagnoni M (2008) ChemSusChem 1:63–66CrossRefGoogle Scholar
  138. 138.
    Martel J, Tessier J, Demoute J-P (1981) Roussel-UCLAF EP 23454 B1Google Scholar
  139. 139.
    Feringa BL, de Lange B (1988) Tetrahedron 44:7213–7222CrossRefGoogle Scholar
  140. 140.
    Moradei O, Paquette LA, Peschko C, Danheiser RL (2003) Org Synth 80:66–73Google Scholar
  141. 141.
    Marinkovic S, Brulé C, Hoffmann N, Prost E, Nuzillard J-M, Bulach V (2004) J Org Chem 69:1646–1651CrossRefGoogle Scholar
  142. 142.
    Fleischer J, Bauer K, Hopp R (1971) DE 2109456 A1Google Scholar
  143. 143.
    Oertling H, Reckziegel A, Bertram H-J (2007) Chem Rev 107:2136–2164CrossRefGoogle Scholar
  144. 144.
    Feringa BL, De Lange B, Jansen JFGA, de Jong JC, Lubben M, Faber W, Schudde EP (1992) Pure Appl Chem 64:1865–1871CrossRefGoogle Scholar
  145. 145.
    Hoffmann N, Bertrand S, Marinkovic S, Pesch J (2006) Pure Appl Chem 78:2227–2246CrossRefGoogle Scholar
  146. 146.
    Griesbeck AG, Hoffmann N, Warzecha K-D (2007) Acc Chem Res 40:128–140CrossRefGoogle Scholar
  147. 147.
    Näsman JH, Johnson AT, White JD (1989) Org Synth 68:162–174Google Scholar
  148. 148.
    Cao R, Liu C, Liu L (1996) Org Prep Proced Int 28:215–216CrossRefGoogle Scholar
  149. 149.
    Badovskaya LA, Latashko VM, Poskonin VV, Grunskaya EP, Tyukhteneva ZI, Rudakova SG, Pestunova SA, Sarkisyan AV (2002) Chem Heterocycl Compd 38:1040–1048CrossRefGoogle Scholar
  150. 150.
    Vinicius M, De Souza N (2005) Mini Rev Org Chem 2:139–145CrossRefGoogle Scholar
  151. 151.
    Carreira EM, Fettes A, Marti C (2006) Org React 67:1–216Google Scholar
  152. 152.
    Denmark SE, Heemstra JR, Beutner GL (2005) Angew Chem Int Ed 44:4682–4698CrossRefGoogle Scholar
  153. 153.
    Casiraghi G, Zanardi F, Appendino G, Rassu G (2000) Chem Rev 100:1929–1972CrossRefGoogle Scholar
  154. 154.
    Pringsheim H, Noth H (1926) Ber Dtsch Chem Ges 53B:114–118Google Scholar
  155. 155.
    Kaufmann WE, Adams R (1923) J Am Chem Soc 45:3029–3044CrossRefGoogle Scholar
  156. 156.
    Huang Z, Qiu L (1992) Shiyou Huagong 21:35–38Google Scholar
  157. 157.
    Wang J, Wang G, Yan W (1998) Jingxi Huagong 15:37–40Google Scholar
  158. 158.
    Lachman I, Spaczynska B (1982) Polish Technol Rev 8–9Google Scholar
  159. 159.
    Bremmer JGM, Keeys RKF (1947) J Chem Soc 1068–1070Google Scholar
  160. 160.
    Wang A, Chen X, Kang H (2000) Huagong Shikau 14:6–8Google Scholar
  161. 161.
    Wojcik BH (1948) J Ind Eng Chem (Washington, DC) 40:210–216CrossRefGoogle Scholar
  162. 162.
    Cho BT, Kang SK, Kim MS, Ryu SR, Duk K (2006) Tetrahedron 62:8164–8168CrossRefGoogle Scholar
  163. 163.
    Naimi-Jamal MR, Mokhtari J, Dekamin MG, Kaupp G (2009) Eur J Org Chem 3567–3572Google Scholar
  164. 164.
    De Vries JG, van Bergen TH, Kellogg RM (1977) Synthesis 246–247Google Scholar
  165. 165.
    Gelbard G, Louis-Andre O, Cherkaoui O (1991) React Polym 15:111–119CrossRefGoogle Scholar
  166. 166.
    Nowicki J, Maciejewski Z (1985) Przemysl Chemiczny 64:20–22Google Scholar
  167. 167.
    Theurillat-Moritz V, Guidi A, Vogel P (1997) Tetrahedron Asymmetry 8:3497–3501CrossRefGoogle Scholar
  168. 168.
    Theurillat-Moritz V, Vogel P (1996) Tetrahedron Asymmetry 7:3163–3168CrossRefGoogle Scholar
  169. 169.
    Jotterand N, Vogel P, Schenk K (1999) Helv Chim Acta 82:821–847CrossRefGoogle Scholar
  170. 170.
    Jotterand N, Vogel P (1999) Tetrahedron Lett 40:5499–5502CrossRefGoogle Scholar
  171. 171.
    Jotterand N, Vogel P (1999) J Org Chem 64:8973–8975CrossRefGoogle Scholar
  172. 172.
    Jotterand N, Vogel P (1999) Synlett 1883–1886Google Scholar
  173. 173.
    Jotterand N, Vogel P (2001) Curr Org Chem 5:637–661CrossRefGoogle Scholar
  174. 174.
    Eschinazi HE (1952) Bull Soc Chim Fr 967–969Google Scholar
  175. 175.
    Tyran LW (1957) US 2776981 19570108. Chem Abstr (1957) 51:43497Google Scholar
  176. 176.
    Aliev Ya Y, Sultanov AS (1959) Khim Khlopchatnika Akad Nauk Uzbek SSR 105–145. Chem Abstr 55:64997Google Scholar
  177. 177.
    Meszaros L, Schobel G (1968) Acta Phys Chem 14:127–137Google Scholar
  178. 178.
    Gardos G, Pechy L, Redey A, Scaszar ME (1976) Hung J Ind Chem 4:125–138Google Scholar
  179. 179.
    Coca J, Morrondo ES, Sastre H (1982) J Chem Technol Biotechnol 32:904–908CrossRefGoogle Scholar
  180. 180.
    Lejemble P, Maire Y, Gaset A, Kalck P (1983) Chem Lett 1403–1406Google Scholar
  181. 181.
    Lejemble P, Gaset A, Kalck P (1984) Biomass 4:263–274CrossRefGoogle Scholar
  182. 182.
    Jung KJ, Gaset A, Molinier J (1988) Biomass 16:89–96CrossRefGoogle Scholar
  183. 183.
    Sugita M, Tsuji H, Okoshi T (2009) PCT Int Appl WO 2009069714 A120090604. Chem Abstr (2009) 150:563626Google Scholar
  184. 184.
    Kalnins P, Hillers S, Tarvid M (1951) Latv PSR Zinat Akad Vestis 443–452Google Scholar
  185. 185.
    Akimoto M, Echigoya E (1977) J Chem Soc Faraday Trans 1 73:193–202CrossRefGoogle Scholar
  186. 186.
    Rivasseau J, Canesson P, Blanchard M (1980) J Phys Chem 84:2791–2795CrossRefGoogle Scholar
  187. 187.
    Mori K, Miyamoto A, Murakami Y (1985) J Catal 95:482–491CrossRefGoogle Scholar
  188. 188.
    Mahaim C, Carrupt P-A, Hagenbuch J-P, Florey A, Vogel P (1980) Helv Chim Acta 63:1149–1157CrossRefGoogle Scholar
  189. 189.
    Metral J-L, Vogel P (1985) Helv Chim Acta 68:334–337CrossRefGoogle Scholar
  190. 190.
    Metral J-L, Lauterwein J, Vogel P (1986) Helv Chim Acta 69:1287–1309CrossRefGoogle Scholar
  191. 191.
    Miller LL, Thomas AD, Wilkins CC, Weil DA (1986) Chem Commun 661–663Google Scholar
  192. 192.
    Thomas AD, Mill LL (1986) J Org Chem 51:4160–4169CrossRefGoogle Scholar
  193. 193.
    Khonke FH, Slawin AMZ, Stoddart JF, Williams DJ (1987) Angew Chem 99:941–943CrossRefGoogle Scholar
  194. 194.
    Ellwood P, Mathias JP, Stoddart JF, Kohnke FH (1988) Bull Soc Chim Belg 97:669–678CrossRefGoogle Scholar
  195. 195.
    Ashton PR, Isaacs NS, Kohnke FH, Stagno D’Alcontres G, Stoddart JF (1989) Angew Chem 101:1269–1271CrossRefGoogle Scholar
  196. 196.
    Ashton PR, Isaacs NS, Kohnke FH, Mathias JP, Stoddart JF (1989) 101:1266–1269Google Scholar
  197. 197.
    Ashton PR, Mathias JP, Stoddart JF (1991) Polymer Prepr 32:419–420CrossRefGoogle Scholar
  198. 198.
    Girreser U, Giuffrida D, Kohnke FH, Mathias JP, Philp D, Stoddart JF (1993) Pure Appl Chem 65:119–125CrossRefGoogle Scholar
  199. 199.
    Ashton PR, Mathias JP, Stoddart JF (1993) Synthesis 65:119–125Google Scholar
  200. 200.
    Ashton PR, Girreser U, Giuffrida D, Kohnke FH, Mathias JP, Raymo FM, Slawin AMZ, Stoddart JF, Williams DJ (1993) J Am Chem Soc 115:5422–5429CrossRefGoogle Scholar
  201. 201.
    Ahston PR, Brown GR, Smith DR, Stoddart JF, Williams DJ (1993) Tetrahedron Lett 34:8337–8340CrossRefGoogle Scholar
  202. 202.
    Ahston PR, Brown GR, Brown GR, Isaacs NS, Giuffrida D, Kohnke FH, Mathias JP, Slawin AMZ, Smith DR, Stoddart JF, Williams DJ (1992) J Am Chem Soc 114:6330–6353CrossRefGoogle Scholar
  203. 203.
    Carrupt P-A, Vogel P (1979) Tetrahedron Lett 19:4533–4536CrossRefGoogle Scholar
  204. 204.
    Bessière Y, Vogel P (1980) Helv Chim Acta 63:232–243CrossRefGoogle Scholar
  205. 205.
    Tamariz J, Vogel P (1984) Tetrahedron 40:4549–4560CrossRefGoogle Scholar
  206. 206.
    Tornare J-M, Vogel P (1985) Helv Chim Acta 68:1069–1077CrossRefGoogle Scholar
  207. 207.
    Dienes Z, Antonsson T, Vogel P (1993) Tetrahedron Lett 34:1013–1016CrossRefGoogle Scholar
  208. 208.
    Dienes Z, Vogel P (1995) Bioorg Med Chem Lett 5:547–550CrossRefGoogle Scholar
  209. 209.
    Vogel P (1998) Curr Org Chem 2:255–280Google Scholar
  210. 210.
    Hoffmann HMR (1972) Angew Chem Int Ed 11:324Google Scholar
  211. 211.
    Noyori R, Makino S, Okita T, Haykawa Y (1975) J Org Chem 40:806–807CrossRefGoogle Scholar
  212. 212.
    Noyori R, Haykawa Y (1983) Org React 29:163–344Google Scholar
  213. 213.
    Sato T, Noyori R (1978) Bull Chem Soc Jpn 51:2745–2746CrossRefGoogle Scholar
  214. 214.
    Rigby JH, Pigge FC (1997) Org React 53:351–478Google Scholar
  215. 215.
    Cowling AP, Mann J, Usmani AA (1981) J Chem Soc Perkin Trans 1:2116–2119CrossRefGoogle Scholar
  216. 216.
    Foehlisch B, Gehrlach E, Herter R (1982) Angew Chem 94:144CrossRefGoogle Scholar
  217. 217.
    Foehlisch B, Gehrlach E, Geywitz B (1987) Chem Ber 120:1815–1824CrossRefGoogle Scholar
  218. 218.
    Vidal-Pascual M, Martinez-Lamenca C, Hoffmann HMR (2006) Org Synth 83:61–69Google Scholar
  219. 219.
    Rashatasakhon P, Harmata M (2009) Tetrahedron Lett 50:2109–2110CrossRefGoogle Scholar
  220. 220.
    Noyori R, Sato T, Hayakawa Y (1978) J Am Chem Soc 100:2561–2563CrossRefGoogle Scholar
  221. 221.
    Sato T, Noyori R (1980) Tetrahedron Lett 21:2535–2538CrossRefGoogle Scholar
  222. 222.
    Noyori R, Sato T, Kobayashi H (1983) Bull Chem Soc Jpn 56:2661–2679CrossRefGoogle Scholar
  223. 223.
    Sato T, Hayakawa Y, Noyori R (1984) Bull Chem Soc Jpn 57:2515–2525CrossRefGoogle Scholar
  224. 224.
    Bunn BH, Cox PJ, Simpkins NS (1983) Tetrahedron 49:207–218CrossRefGoogle Scholar
  225. 225.
    Hoffmann HMR, Dunkel R, Mentzel M, Reuter H, Stark CBW (2001) Chem Eur J 7:4771–4789CrossRefGoogle Scholar
  226. 226.
    Lampe TFJ, Hoffmann HMR (1996) Chem Commun 1931–1932Google Scholar
  227. 227.
    Dunkel R, Hoffmann HMR (1999) Tetrahedron 55:8385–8396CrossRefGoogle Scholar
  228. 228.
    Kim H, Hoffmann HMR (2000) Eur J Org Chem 2195–2201Google Scholar
  229. 229.
    Vakapoulos A, Hoffmann HMR (2001) Org Lett 3:177–180CrossRefGoogle Scholar
  230. 230.
    Bowers KG, Mann J, Walsh EB, Howarth OW (1987) J Chem Soc Perkin Trans 1:1657–1666CrossRefGoogle Scholar
  231. 231.
    Cowling AP, Mann J, Usmani AA (1981) J Chem Soc Perkin Trans 1:2116–2119CrossRefGoogle Scholar
  232. 232.
    Dunkel R, Mentzel M, Hoffmann HMR (1997) Tetrahedron 53:14929–14936CrossRefGoogle Scholar
  233. 233.
    Lee JC, Cho SY, Cha JK (1999) Tetrahedron Lett 40:7675–7678CrossRefGoogle Scholar
  234. 234.
    Rashatasakhon P, Harmata M (2009) Tetrahedron Lett 50:2109–2110CrossRefGoogle Scholar
  235. 235.
    Stark CBW, Pierau S, Wartchaw R, Hoffmann HMR (2000) Chem Eur J 6:684–691CrossRefGoogle Scholar
  236. 236.
    Schwenter ME, Vogel P (2000) Chem Eur J 6:4091–4103CrossRefGoogle Scholar
  237. 237.
    Sharpless KB, Kolb HC, Van Nieuwenhze MS (1994) Chem Rev 94:2483–2547CrossRefGoogle Scholar
  238. 238.
    Schwenter ME, Vogel P (2001) J Org Chem 66:7869–7872CrossRefGoogle Scholar
  239. 239.
    Vogel P, Gerber-Lemaire S, Carmona AT, Meilert KT, Schwenter ME (2005) Pure Appl Chem 77:131–137CrossRefGoogle Scholar
  240. 240.
    Gerber-Lemaire S, Carmona AT, Meilert KT, Vogel P (2006) Eur J Org Chem 891–900Google Scholar
  241. 241.
    Meilert KT, Pettit GR, Vogel P (2004) Helv Chim Acta 87:1493–1507CrossRefGoogle Scholar
  242. 242.
    Gerber-Lemaire S, Vogel P (2004) Eur J Org Chem 5040–5046Google Scholar
  243. 243.
    Favre S, Gerber-Lemaire S, Vogel P (2007) Org Lett 9:5107–5110CrossRefGoogle Scholar
  244. 244.
    Reymond J-L, Vogel P (1990) Tetrahedron Asymmetry 1:729–736CrossRefGoogle Scholar
  245. 245.
    Forster A, Kovac T, Mosimann H, Renaud P, Vogel P (1999) Tetrahedron Asymmetry 10:567–571CrossRefGoogle Scholar
  246. 246.
    Vogel P, Cossy J, Plumet J, Arjona O (1999) Tetrahedron 55:12521–13642CrossRefGoogle Scholar
  247. 247.
    Warm A, Vogel P (1986) J Org Chem 51:5348–5353CrossRefGoogle Scholar
  248. 248.
    Vogel P, Fattori D, Gasparini F, LeDrian C (1990) Synlett 173–185Google Scholar
  249. 249.
    Vogel P (2001) De novo synthesis of monosaccharides. In: Fraser-Reid B, Tatsuka K, Thiem J (eds) Glycoscience II. Springer, Heidelberg, pp 1023–1179, Chapter 4.4Google Scholar
  250. 250.
    Vogel P (2006) Organic synthesis of sugars. CRC Press LLC, Boca Raton, FL, pp 629–725Google Scholar
  251. 251.
    De Guchteneere E, Fattori D, Vogel P (1992) Tetrahedron 48:10603–10620CrossRefGoogle Scholar
  252. 252.
    Fattori D, Vogel P (1992) Tetrahedron 48:10587–10602CrossRefGoogle Scholar
  253. 253.
    Durgnat J-M, Vogel P (1993) Helv Chim Acta 76:222–240CrossRefGoogle Scholar
  254. 254.
    Huenenberger P, Allemann S, Vogel P (1994) Carbohydr Res 157:175–187CrossRefGoogle Scholar
  255. 255.
    Auberson Y, Vogel P (1989) Angew Chem 101:1554–1555CrossRefGoogle Scholar
  256. 256.
    Wagner J, Vogel P (1991) Tetrahedron Lett 32:3169–3170CrossRefGoogle Scholar
  257. 257.
    Wagner J, Vogel P (1991) Tetrahedron 47:9641–9648CrossRefGoogle Scholar
  258. 258.
    Baudat A, Picasso S, Vogel P (1996) Carbohydr Res 281:277–284CrossRefGoogle Scholar
  259. 259.
    Emery F, Vogel P (1994) J Carbohydr Chem 13:555–563CrossRefGoogle Scholar
  260. 260.
    Pechy P, Gasparini F, Vogel P (1992) Synlett 676–678Google Scholar
  261. 261.
    Jeanneret V, Gasparini F, Pechy P, Vogel P (1992) Tetrahedron 48:10637–10644CrossRefGoogle Scholar
  262. 262.
    LeDrian C, Vieira E, Vogel P (1989) Helv Chim Acta 72:338–347CrossRefGoogle Scholar
  263. 263.
    LeDrian C, Vionnet J-P, Vogel P (1990) Helv Chim Acta 73:161–168CrossRefGoogle Scholar
  264. 264.
    Allemann S, Vogel P (1994) Helv Chim Acta 77:1–9CrossRefGoogle Scholar
  265. 265.
    Lysek R, Schuetz C, Vogel P (2005) Bioorg Med Chem Lett 15:3071–3075CrossRefGoogle Scholar
  266. 266.
    Lysek R, Schuetz C, Vogel P (2005) Helv Chim Acta 88:2733–2768CrossRefGoogle Scholar
  267. 267.
    Lysek R, Favre S, Vogel P (2007) Tetrahedron 63:6558–6572CrossRefGoogle Scholar
  268. 268.
    Jeganathan S, Vogel P (1991) Carbohydr Res 222:151–161CrossRefGoogle Scholar
  269. 269.
    Emery F, Vogel P (1995) J Org Chem 60:5843–5854CrossRefGoogle Scholar
  270. 270.
    Wagner J, Vogel P (1989) Chem Commun 1634–1635Google Scholar
  271. 271.
    Neff D, Chen Y, Vogel P (1991) Helv Chim Acta 74:508–516CrossRefGoogle Scholar
  272. 272.
    Chen Y, Vogel P (1992) Tetrahedron Lett 33:4917–4920Google Scholar
  273. 273.
    Chen Y, Vogel P (1994) J Org Chem 59:2487–2496CrossRefGoogle Scholar
  274. 274.
    Reymond J-L, Pinkerton AA, Vogel P (1991) J Org Chem 56:2128–2135CrossRefGoogle Scholar
  275. 275.
    Bimwala RM, Vogel P (1992) J Org Chem 57:2076–2083CrossRefGoogle Scholar
  276. 276.
    Ferritto R, Vogel P (1994) Tetrahedron Asymmetry 5:2077–2092CrossRefGoogle Scholar
  277. 277.
    Ferritto R, Vogel P (1995) Tetrahedron Lett 36:3517–3518CrossRefGoogle Scholar
  278. 278.
    Cossy J, Ranaivosata J-L, Bellosta V, Ancerewicz J, Ferritto R, Vogel P (1995) J Org Chem 60:8351–8359CrossRefGoogle Scholar
  279. 279.
    Ferritto R, Vogel P (1996) Synlett 281–282Google Scholar
  280. 280.
    Baudat A, Vogel P (1996) Tetrahedron Lett 37:483–484CrossRefGoogle Scholar
  281. 281.
    Frerot E, Marquis C, Vogel P (1996) Tetrahedron Lett 37:2023–2026CrossRefGoogle Scholar
  282. 282.
    Kraehenbuehl K, Picasso S, Vogel P (1997) Bioorg Med Chem Lett 7:893–896CrossRefGoogle Scholar
  283. 283.
    Baudat A, Vogel P (1997) J Org Chem 62:6252–6260CrossRefGoogle Scholar
  284. 284.
    Marquis C, Picasso S, Vogel P (1999) Synthesis 1441–1452Google Scholar
  285. 285.
    Warm A, Vogel P (1987) Helv Chim Acta 70:690–700CrossRefGoogle Scholar
  286. 286.
    Moritz V, Vogel P (1992) Tetrahedron Lett 33:5243–5244CrossRefGoogle Scholar
  287. 287.
    Takayama H, Iyobe A, Koizumi T (1986) Chem Commun 771–772Google Scholar
  288. 288.
    Corey EJ, Loh TP (1993) Tetrahedron Lett 34:3979–3982CrossRefGoogle Scholar
  289. 289.
    Akai S, Naka T, Omura S, Tanimoto K, Imanashi M, Takebe Y, Matsugi M, Kita Y (2002) Chem Eur J 8:4255–4264CrossRefGoogle Scholar
  290. 290.
    Tojo S, Isobe M (2005) Synthesis 1237–1244Google Scholar
  291. 291.
    Guan YK, Li YL (2005) Chirality 17:113–118CrossRefGoogle Scholar
  292. 292.
    Ryu DH, Kim KH, Sim JY, Corey EJ (2007) Tetrahedron Lett 48:5735–5737CrossRefGoogle Scholar
  293. 293.
    Sakakura A, Kondo R, Matsumura Y, Akakura M, Ishihara K (2009) J Am Chem Soc 131:17762–17764CrossRefGoogle Scholar
  294. 294.
    Mukaiyama T, Iwasawa N (1981) Chem Lett 29–32Google Scholar
  295. 295.
    Acena JL, Arjona O, Plumet J (1996) Tetrahedron Asymmetry 7:3535–3544CrossRefGoogle Scholar
  296. 296.
    Arjona O, Iradier F, Medel R, Plumet J (1999) Tetrahedron Asymmetry 10:3431–3442CrossRefGoogle Scholar
  297. 297.
    Acena JL, Arjona O, Leon MA, Plumet J (2000) Org Lett 2:3683–3686CrossRefGoogle Scholar
  298. 298.
    Arjona O, Menchaca R, Plumet J (2001) Tetrahedron 57:6751–6755CrossRefGoogle Scholar
  299. 299.
    Arjona O, Menchaca R, Plumet J (2001) Org Lett 3:107–108CrossRefGoogle Scholar
  300. 300.
    Schindler CS, Carreira EM (2009) Chem Soc Rev 38:3222–3241CrossRefGoogle Scholar

Copyright information

© Springer 2010

Authors and Affiliations

  • Frédéric Martel
    • 1
  • Boris Estrine
    • 1
  • Richard Plantier-Royon
    • 2
  • Norbert Hoffmann
    • 2
  • Charles Portella
    • 2
  1. 1.Agro Industrie Recherches et DéveloppementsPomacleFrance
  2. 2.UFR Sciences Exactes et Naturelles, CNRS UMR 6229Institut de Chimie Moléculaire de Reims, Université de Reims Champagne-ArdenneReims Cedex 2France

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