Chemoenzymatic synthesis of inositols, conduritols, and cyclitol analogues

Chemical Reviews

Volumn 111, Issue 7, 2011, Pages 4223-4258

  Duchek, Jan ^a   Adams, David R ^a   Hudlicky, Tomas ^a  

^a BROCK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARTIFICIAL ENZYMES; CHEMO-ENZYMATIC SYNTHESIS; CONDURITOLS; CYCLITOLS; DESYM-METRIZATION; ENZYMATIC RESOLUTIONS; ENZYME MECHANISM; INOSITOL PHOSPHATE; ITERATIVE COUPLING; RACEMIC MIXTURES; TETRAMERS;

ENZYMES; OLIGOMERS; SUGARS;

ALCOHOLS;

CYCLITOL; CYCLOHEXENE DERIVATIVE; DRUG DERIVATIVE; INOSITOL;

BACTERIUM; BIOCATALYSIS; CHEMISTRY; ENZYMOLOGY; FUNGUS; REVIEW; SYNTHESIS;

BACTERIA; BIOCATALYSIS; CYCLITOLS; CYCLOHEXENES; FUNGI; INOSITOL;

EID: 79960604537     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr1004138     Document Type: Review

References (207)

1. IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature. Nomenclature of Cyclitols. 1973 Recommendations. Pure Appl. Chem. 1974, 37, 285.
2. Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: London, 1995; Vol. 1, p 271.
3. Hudlicky, T. Chem. Rev. 1996, 96, 3
4. Evidente, A.; Kornienko, A. Phytochem. Rev. 2009, 8, 449
5. Kornienko, A.; Evidente, A. Chem. Rev. 2008, 108, 1982
6. Di Paolo, G.; De Camilli, P. Nature 2006, 443, 651
7. Rohloff, J. C.; Kent, K. M.; Postich, M. J.; Becker, M. W.; Chapman, H. H.; Kelly, D. E.; Lew, W.; Louie, M. S.; McGee, L. R.; Prisbe, E. J.; Schultze, L. M.; Yu, R. H.; Zhang, L. J. Org. Chem. 1998, 63, 4545
8. Mehta, G.; Ramesh, S. S. Can. J. Chem. 2005, 83, 581
9. Hudlicky, T.; Abboud, K. A.; Bolonick, J.; Maurya, R.; Stanton, M. L.; Thorpe, A. J. Chem. Commun. 1996, 15, 1717
10. See the thematic issue of Biochem. Soc. Symp. 2007, 74.
11. Michell, R. H. Nat. Rev. Mol. Cell Biol. 2008, 9, 151
12. Selected reviews: Posternak, T. The Cyclitols; Holden-Day Publishers: San Francisco, CA, 1965, (revised version of the original Les Cyclitols published by Hermann, Paris, 1962).
13. Billington, D. C. Chem. Soc. Rev. 1989, 18, 83
14. Lysek, R.; Vogel, P. Tetrahedron 2006, 62, 2733
15. Gültekin, M. S.; Çelik, M.; Balci, M. Curr. Org. Chem. 2004, 8, 1159
16. Balci, M. Pure Appl. Chem. 1997, 69, 97
17. Singleton, J.; Hoberg, J. O. Mini Rev. Org. Chem. 2009, 6, 1
18. Kiddle, J. J. Chem. Rev. 1995, 95, 2189
19. Hudlicky, T.; Cebulak, M. Cyclitols and Their Derivatives. A Handbook of Physical, Spectral and Synthetic Data; VCH Publishers: New York, 1993.
20. Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195
21. Scherer Justus Liebigs Ann. Chem. 1850, 73, 322
22. Maquenne Ann. Chim. Phys. 1887, 12, 80
23. Posternak, S.; Posternak, T. Helv. Chim. Acta 1929, 12, 1165
24. Posternak, T. Helv. Chim. Acta 1935, 18, 1283
25. Anderson, R. J. J. Biol. Chem. 1914, 18, 441
26. Posternak, T. Helv. Chim. Acta 1942, 25, 746
27. Dangschat, G. Naturwissenschaften 1942, 30, 146
28. Wieland, H.; Wishart, R. S. Ber. Dtsch. Chem. Ges. 1914, 47, 2082
29. Nietzki, R.; Benckiser, T. Ber. Dtsch. Chem. Ges. 1885, 18, 499
30. Berthelot, M. Leçons sur les méthodes géné rales de synthèse en chimie organique; Gauthier-Villars: Paris, 1864; pp 308-309.
31. Berthelot, M. C. R. Acad. Sci. 1866, 62, 905
32. Berthelot, M. Justus Liebigs Ann. Chem. 1866, 139, 272
33. Nietzki, R.; Benckiser, T. Ber. Dtsch. Chem. Ges. 1885, 18, 1833
34. Büchner, W.; Weiss, E. Helv. Chim. Acta 1964, 47, 1415
35. Grosheintz, J. M.; Fischer, H. O. L. J. Am. Chem. Soc. 1948, 70, 1476
36. Grosheintz, J. M.; Fischer, H. O. L. J. Am. Chem. Soc. 1948, 70, 1479
37. Posternak, T. Helv. Chim. Acta 1950, 23, 1597
38. Hoffmann-Ostenhof, O.; Pittner, F. Can. J. Chem. 1982, 60, 1863
39. Iselin, B. M. J. Am. Chem. Soc. 1949, 71, 3822
40. Kluyver, A. J.; Boezaardt, A. G. J. Rec. Trav. Chim. 1939, 58, 956
41. Fleury, P.; Desjobert, A.; Lecocq, J. Bull. Soc. Chim. Biol. 1954, 36, 1301
42. Brown, D. M.; Hall, G. E. J. Chem. Soc. 1959, 357
43. Pizer, F. L.; Ballou, C. E. J. Am. Chem. Soc. 1959, 81, 915
44. Mehta, G.; Senaiar, R. S.; Bera, M. K. Chem.-Eur. J. 2003, 9, 2264
45. Baran, A.; Balci, M. J. Org. Chem. 2009, 74, 88
46. Berridge, M. J. Nature 1993, 361, 315
47. Streb, H; Irvine, R. F.; Berridge, M. J.; Schulz, I. Nature 1983, 306, 67
48. Riley, A. M.; Murphy, C. T.; Lindley, C. J.; Westwick, J.; Potter, B. V. L. Bioorg. Med. Chem. Lett. 1996, 6, 2197
49. Jenkins, D. J.; Riley, A. M.; Potter, B. V. L. J. Org. Chem. 1996, 61) 7719
50. Walker, N.; Wiltshire, G. H. J. Gen. Microbiol. 1953, 8, 273
51. Gibson, D. T.; Koch, J. R.; Kallio, R. E. Biochemistry 1968, 7, 2653
52. Gibson, D. T.; Koch, J. R.; Schuld, C. L.; Kallio, R. E. Biochemistry 1968, 7, 3795
53. Ballard, D. G. H.; Courtis, A.; Shirley, I. M.; Taylor, S. C. J. Chem. Soc., Chem. Commun. 1983, 17, 954
54. Ley, S. V.; Sternfeld, F.; Taylor, S. Tetrahedron Lett. 1987, 28, 225
55. See: Taylor, S. C. In Enzymes in Organic Synthesis; Ciba Foundation Symposium 111; Pitman: London, 1985; pp 71-74.
56. Ley, S. V.; Sternfeld, F. Tetrahedron Lett. 1988, 29, 5305
57. Ley, S. V.; Parra, M.; Redgrave, A. J.; Sternfeld, F.; Vidal, A. Tetrahedron Lett. 1989, 30, 3557
58. Hudlicky, T.; Luna, H.; Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735
59. For reviews and application to the synthesis of natural products, see: Hudlicky, T.; Reed, J. W. Chem. Soc. Rev. 2009, 38, 3117
60. Hudlicky, T.; Reed, J. W. Synlett 2009, 5, 685
61. Johnson, R. A. Microbial Arene Oxidations; Overman, L. E., Ed.; Organic Reactions; John Wiley & Sons: New York, 2004; Vol. 63, pp 117-264.
62. Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichim. Acta 1999, 32, 35
63. Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc. 1990, 112, 9439
64. For a discussion of this concept, see: Hudlicky, T.; Reed, J. W. The Way of Synthesis; Wiley-VCH: Weinheim, Germany, 2007; pp 146-154.
65. For a discussion of these design concepts, see: Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: London, 1993; Vol. 2, p 113.
66. References 2a, 2b, 10, 41a, 41b, 41d, and 43.
67. Carless, H. A. J.; Busia, K.; Oak, O. Z. Synlett 1993, 9, 672
68. Mandel, M.; Hudlicky, T.; Kwart, L. D.; Whited, G. M. J. Org. Chem. 1993, 58, 2331
69. Hudlicky, T.; Mandel, M.; Rouden, J.; Lee, R. S.; Bachmann, B.; Dudding, T.; Yost, K.; Merola, J. S. J. Chem. Soc., Perkin Trans. 1 1994, 1553
70. Mandel, M.; Hudlicky, T. J. Chem. Soc., Perkin Trans. 1 1993, 7, 741
71. Mandel, M.; Hudlicky, T. J. Chem. Soc., Perkin Trans. 1 1993, 13, 1537
72. Desjardins, M.; Brammer, L. E., Jr.; Hudlicky, T. Carbohydr. Res. 1997, 304, 39
73. Brammer, L. E., Jr.; Hudlicky, T. Tetrahedron: Asymmetry 1998, 9, 2011
74. For a definition and examples of redundant operations, see ref 43, Chapter 2, pp 107-109.
75. Hudlicky, T.; Restrepo-Sánchez, N.; Kary, P. D.; Jaramillo-Gómez, L. M. Carbohydr. Res. 2000, 324, 200
76. Vitelio, C.; Bellomo, A.; Brovetto, M.; Seoane, G.; Gonzalez, D. Carbohydr. Res. 2004, 339, 1773
77. Carless, H. A. J.; Billinge, J. R.; Oak, O. Z. Tetrahedron Lett. 1989, 30, 3113
78. Boyd, D. R.; Dorrity, M. R. J.; Hand, M. V.; Malone, J. F.; Sharma, N. D.; Dalton, H.; Gray, D. J.; Sheldrake, G. N. J. Am. Chem. Soc. 1991, 113, 666
79. Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 2, 61
80. Le Drian, C.; Vieira, E.; Vogel, P. Helv. Chim. Acta 1989, 72, 338
81. Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 15, 1006
82. Sütbeyaz, Y.; Seçen, H.; Balci, M. J. Chem. Soc., Chem. Commun. 1988, 19, 1330
83. Hudlicky, T.; Price, J. D.; Olivo, H. F. Synlett 1991, 9, 645
84. Carless, H. A. J. Tetrahedron Lett. 1992, 33, 6379
85. Carless, H. A. J. J. Chem. Soc., Chem. Commun. 1992, 3, 234
86. Finn, K. J.; Collins, J.; Hudlicky, T. Tetrahedron 2006, 62, 7471
87. Allen, C. C. R.; Boyd, D. R.; Dalton, H.; Sharma, N. D.; Brannigan, I.; Kerley, N. A.; Sheldrake, G. N.; Taylor, S. C. J. Chem. Soc., Chem. Commun. 1995, 2, 117
88. Boyd, D. R.; Sharma, N. D.; Hand, M. V.; Groocock, M. R.; Kerley, N. A.; Dalton, H.; Chima, J.; Sheldrake, G. N. J. Chem. Soc., Chem. Commun. 1993, 11, 974
89. Johnson, C. R.; Adams, J. P.; Collins, M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1, 1
90. Akgün, H.; Hudlicky, T. Tetrahedron Lett. 1999, 40, 3081
91. Khan, M. A.; Lowe, J. P.; Johnson, A. L.; Steward, A. J. W.; Lewis, S. E. Chem. Commun. 2011, 47, 215
92. Magnet, S.; Blanchard, J. S. Chem. Rev. 2005, 105, 477
93. Durante-Mangoni, E.; Grammaticos, A.; Utili, R.; Falagas, M. E. Int. J. Antimicrob. Agents 2009, 33, 201
94. Werbitzky, O.; Klier, K.; Felber, H. Liebigs Ann. Chem. 1990, 3, 267
95. Schürrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc., Perkin Trans. 1 1991, 10, 2407
96. Hudlicky, T; Olivo, H. F. Tetrahedron Lett. 1991, 32, 6077
97. Johnson, C. R.; Plé, P. A.; Su, L.; Heeg, M. J.; Adams, J. P. Synlett 1992, 5, 388
98. Seçen, H.; Gültekin, S.; Sütbeyaz, Y.; Balci, M. Synth. Commun. 1994, 24, 2103
99. Bellomo, A.; Giacomini, C.; Brena, B.; Seoane, G.; Gonzalez, D. Synth. Commun. 2007, 37, 3509
100. Banwell, M. G.; Haddad, N.; Hudlicky, T.; Nugent, T. C.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1997, 12, 1779
101. Rinner, U.; Hudlicky, T. Synlett 2005, 3, 365
102. Chapleur, Y; Chrétien, F.; Ahmed, I. S.; Khaldi, M. Curr. Org. Synth. 2006, 3, 341
103. Jin, Z. Nat. Prod. Rep. 2009, 26, 363
104. Hudlicky, T.; Olivo, H. F. J. Am. Chem. Soc. 1992, 114, 9694
105. Tian, X.; Hudlicky, T.; Königsberger, K. J. Am. Chem. Soc. 1995, 117, 3643
106. Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752
107. Rinner, U.; Hudlicky, T.; Gordon, H.; Pettit, G. R. Angew. Chem., Int. Ed. 2004, 43, 5342
108. Rinner, U.; Siengalewicz, P.; Hudlicky, T. Org. Lett. 2002, 4, 115
109. Hudlicky, T.; Rinner, U.; Gonzalez, D.; Akgun, H.; Schilling, S.; Siengalewicz, P.; Martinot, T. A.; Pettit, G. R. J. Org. Chem. 2002, 67, 8726
110. Gonzalez, D.; Martinot, T.; Hudlicky, T. Tetrahedron Lett. 1999, 40, 3077
111. Matveenko, M.; Kokas, O. J.; Banwell, M. G.; Willis, A. C. Org. Lett. 2007, 9, 3683
112. Matveenko, M.; Banwell, M. G.; Willis, A. C. Tetrahedron 2008, 64, 4817
113. Moser, M.; Sun, X.; Hudlicky, T. Org. Lett. 2005, 7, 5669
114. Hudlicky, T.; Moser, M.; Banfield, S. C.; Rinner, U.; Chapuis, J.-C.; Pettit, G. R. Can. J. Chem. 2006, 84, 1313
115. Collins, J.; Drouin, M.; Sun, X.; Rinner, U.; Hudlicky, T. Org. Lett. 2008, 10, 361
116. Collins, J.; Rinner, U.; Moser, M.; Hudlicky, T.; Ghiviriga, I.; Romero, A. E.; Kornienko, A.; Ma, D.; Griffin, C.; Pandey, S. J. Org. Chem. 2010, 75, 3069
117. Carless, H. A. J.; Oak, O. Z. Tetrahedron Lett. 1991, 32, 1671
118. Banwell, M. G.; Bray, A. M.; Wong, D. J. New J. Chem. 2001, 25, 1351
119. Yamada, T.; Iritani, M.; Ohishi, H.; Tanaka, K.; Minoura, K.; Doi, M.; Numata, A. Org. Biomol. Chem. 2007, 5, 3979
120. Donohoe, T. J.; Blades, K.; Helliwell, M.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1998, 39, 8755
121. Boyd, D. R.; Sharma, N. D.; Acaru, C. A.; Malone, J. F.; O'Dowd, C. R.; Allen, C. C. R.; Stevenson, P. J. Org. Lett. 2010, 12, 2206
122. Ley, S. V.; Yeung, L. L. Synlett 1992, 4, 291
123. Entwistle, D. A.; Hudlicky, T. Tetrahedron Lett. 1995, 36, 2591
124. Boyd, D. R.; Sharma, N. D.; Llamas, N. M.; Malone, J. F.; O'Dowd, C. R.; Allen, C. C. R. Org. Biomol. Chem. 2005, 3, 1953
125. Fabris, F.; Collins, J.; Sullivan, B.; Leisch, H.; Hudlicky, T. Org. Biomol. Chem. 2009, 7, 2619
126. Asano, N. Glycobiology 2003, 13, 93R
127. Kobayashi, Y. Carbasugars: Synthesis and Functions In Glycoscience; Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2008; pp 1913-1997.
128. Arjona, O., Gómez, A. M., López, J. C., and Plumet, J. Chem. Rev. 2007, 107, 1919
129. Carless, H. A. J.; Dove, Y. Tetrahedron: Asymmetry 1996, 7, 649
130. Oppong, K. A.; Hudlicky, T.; Yan, F.; York, C.; Nguyen, B. V. Tetrahedron 1999, 55, 2875
131. Nguyen, B. V.; York, C.; Hudlicky, T. Tetrahedron 1997, 53, 8807
132. Oppong, K. A.; Hudlicky, T.; Yan, F.; York, C.; Nguyen, B. V. Tetrahedron 1999, 55, 2875
133. Yan, F.; Nguyen, B. V.; York, C.; Hudlicky, T. Tetrahedron 1997, 53, 11541
134. Lallemand, M.-C.; Desjardins, M.; Freeman, S.; Hudlicky, T. Tetrahedron Lett. 1997, 38, 7693
135. Desjardins, M.; Lallemand, M.-C.; Hudlicky, T.; Abboud, K. A. Synlett 1997, 6, 728
136. Bellomo, A.; Caramano, S.; Rossini, C.; Gonzalez, D. Carbohydr. Res. 2009, 344, 44
137. Bellomo, A.; Bertucci, A.; Stefani, H.; Vázquez, A.; Gonzalez, D. Tetrahedron: Asymmetry 2009, 20, 2673
138. Bellomo, A.; Gonzalez, D. Tetrahedron: Asymmetry 2006, 17, 474
139. Bellomo, A.; Gonzalez, D.; Stefani, H. A. J. Organomet. Chem. 2008, 693, 1136
140. Bellomo, A.; Weber, M.; Gonzalez, D.; Stefani, H. A. Catal. Commun. 2009, 10, 1647
141. de la Sovera, V., Bellomo, A., Pena, J. M., Gonzalez, D., and Stafani, H. A. Mol. Divers. 2011, 15, 163
142. Bellomo, A.; Gonzalez, D. Tetrahedron Lett. 2007, 48, 3047
143. Ley, S. V.; Yeung, L. L. Synlett 1992, 12, 997
144. Bellomo, A.; Bonilla, J. B.; López-Prados, J.; Martín-Lomas, M.; Gonzalez, D. Tetrahedron: Asymmetry 2009, 20, 2061
145. Shie, J.-J.; Fang, J.-M.; Wong, C.-H. Angew. Chem., Int. Ed. 2008, 47, 5788
146. Matveenko, M.; Willis, A. C.; Banwell, M. G. Tetrahedron Lett. 2008, 49, 7018
147. Sullivan, B.; Carrera, I.; Drouin, M.; Hudlicky, T. Angew. Chem., Int. Ed. 2009, 48, 4229
148. Werner, L.; Machara, A.; Hudlicky, T. Adv. Synth. Catal. 2010, 352, 195
149. Shie, J.-J; Fang, J.-M; Wang, S.-Y; Tsai, K.-C.; Cheng, Y.-S. E.; Yang, A.-S.; Hsiao, S.-C.; Su, C.-Y.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 11892
150. Yamatsugu, K.; Yin, L.; Kamijo, S.; Kimura, Y.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2009, 48, 1070
151. Yeung, Y.-Y.; Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 6310
152. Magasanik, B.; Chargaff, E. J. Biol. Chem. 1948, 174, 173
153. Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook; Drauz, K.; Waldman, H., Eds.; Wiley-VCH: Weinheim, Germany, 2002.
154. Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Baldwin, J. E.; Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series; Pergamon Press: Oxford, U.K., 1994; Vol. 12.
155. García-Urdiales, E.; Alfonso, I.; Gotor, V. Chem. Rev. 2005, 105, 313
156. Johnson, C. R.; Adams, J. P.; Bis, S. J.; De Jong, R. L.; Golebiowski, A.; Medich, J. R.; Penning, T. D.; Senanayake, C. H.; Steensma, D. H.; Van Zandt, M. C. Pure. Appl. Chem. 1992, 64, 1115
157. See, for example: Ling, L.; Watanabe, Y.; Akiyama, T.; Ozaki, S. Tetrahedron Lett. 1992, 33, 1911
158. Klibanov, A. M. Nature 2001, 409, 241
159. Kobayashi, S.; Kamiyama, K.; Ohno, M. J. Org. Chem. 1990, 55, 1169
160. Kobayashi, S.; Kamiyama, K.; Iimori, T.; Ohno, M. Tetrahedron Lett. 1984, 25, 2557
161. Pingli, L.; Vandewalle, M. Tetrahedron 1994, 50, 7061
162. Liu, P.; Vandewalle, M. Tetrahedron Lett. 1993, 34, 3625
163. Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 3, 243
164. Dumortier, L.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 3, 245
165. Pingli, L.; Vandewalle, M. Synlett 1994, 4, 228
166. Suemune, H.; Matsuno, K.; Uchida, M.; Sakai, K. Tetrahedron: Asymmetry 1992, 3, 297
167. Sanfilippo, C.; Patti, A.; Piattelli, M.; Nicolosi, G. Tetrahedron: Asymmetry 1997, 8, 1569
168. Spielvogel, D.; Kammerer, J.; Keller, M.; Prinzbach, H. Tetrahedron Lett. 2000, 41, 7863
169. Gültekin, M. S.; Çelik, M.; Turkut, E.; Tanyeli, C.; Balci, M. Tethahedron: Asymmetry 2004, 15, 453
170. Johnson, C. R.; Miller, M. W. J. Org. Chem. 1995, 60, 6674
171. Adelt, S.; Plettenburg, O; Stricker, R.; Reiser, G.; Altenbach, H.-J.; Vogel, G. J. Med. Chem. 1999, 42, 1262
172. Podeschwa, M.; Plettenburg, O.; vom Brocke, J.; Block, O.; Adelt, S.; Altenbach, H.-J. Eur. J. Org. Chem. 2003, 10, 1958
173. Podeschwa, M. A. L.; Plettenburg, O.; Altenbach, H.-J. Eur. J. Org. Chem. 2005, 14, 3101
174. Podeschwa, M. A. L.; Plettenburg, O.; Altenbach, H.-J. Eur. J. Org. Chem. 2005, 14, 3116
175. Podeschwa, M. A. L.; Plettenburg, O.; Altenbach, H.-J. Org. Biomol. Chem. 2003, 1, 1919
176. Kwon, Y.-U.; Changgook, L.; Chung, S.-K. J. Org. Chem. 2002, 67, 3327
177. Seo, K.-C.; Yu, S.-H.; Chung, S.-K. J. Carbohydr. Chem. 2007, 26, 305
178. Patti, A.; Sanfilippo, C.; Piattelli, M.; Nicolosi, G. Tetrahedron: Asymmetry 1996, 7, 2665
179. Oguzkaya, F.; Sahin, E.; Tanyeli, C. Tetrahedron: Asymmetry 2006, 17, 3004
180. Gümüs, A.; Tanyeli, C. Helv. Chim. Acta 2010, 93, 1882
181. D'Antona, N.; Nicolosi, G.; Morrone, R.; Kubác, D.; Kaplan, O.; Martínková, L. Tetrahedron: Asymmetry 2010, 21, 695
182. Selected examples: Baudin, G.; Glänzer, B. I.; Swaminathan, K. S; Vasella, A. Helv. Chim. Acta 1988, 71, 1367
183. Liu, Y.-C.; Chen, C.-S. Tetrahedron Lett. 1989, 30, 1617
184. Ling, L.; Ozaki, S. Carbohydr. Res. 1994, 256, 49
185. Laumen, K.; Ghisalba, O. Biosci. Biotechnol. Biochem. 1994, 58, 2046
186. Chung, S.-K.; Kwon, Y.-U; Shin, J.-H.; Chang, Y.-T.; Lee, C.; Shin, B.-G.; Kim, K.-C.; Kim, M.-J. J. Org. Chem. 2002, 67, 5626
187. Chung, S.-K; Chang, Y.-T.; Lee, E. J.; Shin, B.-G; Kwon, Y.-U; Kim, K.-C.; Lee, D. H.; Kim, M.-J. Bioorg. Med. Chem. Lett. 1998, 8, 1503
188. Adelt, S.; Plettenburg, O; Dallmann, G.; Ritter, F. P.; Shears, S. B.; Altenbach, H.-J.; Vogel, G. Bioorg. Med. Chem. Lett. 2001, 11, 2705 See also Plettenburg, O.; Adelt, S.; Vogel, G.; Altenbach, H.-J. Tetrahedron: Asymmetry 2000, 11, 1057
189. Gorin, P. A. J.; Horitsu, K.; Spencer, J. F. T. Can. J. Chem. 1965, 43, 2259
190. Hart, J.; Falshaw, A.; Farkas, E.; Thiem, J. Synlett 2001, 3, 329
191. Hart, J. B.; Kröger, L.; Falshaw, A.; Falshaw, R.; Farkas, E.; Thiem, J.; Win, A. L. Carbohydr. Res. 2004, 339, 1857
192. Miranda-Molina, A.; López-Munguía, A.; Román, M. L. S.; Escalante, J.; Leyva, M. A.; Puebla, A. M.; Castillo, E.; Álvarez, L. Tetrahedron: Asymmetry 2010, 21, 43
193. See, for example: Enzyme Catalysis in Organic Synthesis; Drauz, K.; Waldmann, H., Eds.; Wiley-VCH: Weinheim, Germany, 1995; Vol. II, pp 547-593.
194. See ref 118 b, pp 195-251.
195. Schmid, W.; Whitesides, G. M. J. Am. Chem. Soc. 1990, 112, 9670
196. Chou, W.-C.; Fotsch, C.; Wong, C.-H. J. Org. Chem. 1995, 60, 2916
197. Blidi, L. E.; Crestia, D.; Gallienne, E.; Demuynck, C.; Bolte, J.; Lemaire, M. Tetrahedron: Asymmetry 2004, 15, 2951
198. Gijsen, H. J. M.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 7057
199. Bui, V. P.; Hudlicky, T. Tetrahedron 2004, 60, 641
200. Paul, B. J.; Martinot, T. A.; Willis, J.; Hudlicky, T. Synthesis 2001, 6, 952
201. Paul, B. J.; Willis, J.; Martinot, T. A.; Ghiviriga, I.; Abboud, K. A.; Hudlicky, T. J. Am. Chem. Soc. 2002, 124, 10416
202. Hudlicky, T.; Abboud, K. A.; Entwistle, D. A.; Fan, R.; Maurya, R.; Thorpe, A. J.; Bolonick, J.; Myers, B. Synthesis 1996, 7, 897
203. Hudlicky, T.; Thorpe, A. J. Chem. Commun. 1996, 17, 1993
204. Pirrung, M. C. Chem. Biol. 1999, 6, R167
205. Sculimbrene, B. R.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 10125
206. Note added in proof: As this review went to press, two noteworthy publications appeared. Lewis and co-workers reported a chemoenzymatic synthesis of new inositol-amino acid hybrid structures: Pilgrim, S., Kociok-Köhn, G., Lloyd, M. D., and Lewis, S. E. Chem. Commun. 2011, 47, 4799
207. In addition, Gonzalez and co-workers reported a chemoenzymatic approach towards triazolic analogs of pancratistatin: de la Sovera, V.; Bellomo, A.; Gonzalez, D. Tetrahedron Lett. 2011, 52, 430