The enterprise of synthesis: From concept to practice

Journal of Organic Chemistry

Volumn 77, Issue 16, 2012, Pages 6657-6688

  Hanessian, Stephen ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON FRAMEWORK; CHIRAL SYNTHONS; HYDROXY ACIDS; NATURAL PRODUCTS; NATURALLY OCCURRING; PERSONAL RESEARCH; SYNTHETIC METHODS; TARGET MOLECULE;

AMINO ACIDS; CARBOHYDRATES; CARBOXYLIC ACIDS; OLEFINS;

STEREOCHEMISTRY;

ALKENE; ALKYNE; AMBRUTICIN S; AMINO ACID; AVERMECTIN B1 A; BAFILOMYCIN A1; BORRELIDIN; BROMINE; CARBOHYDRATE; CARBON; CHLORODYSINOSIN A; CHOLORDYSINOSIN A; DIHYDROMEVINOLIN; DYSINOSIN A; HYDROXYACID; IONOMYCIN; JERANGOLID A; MORPHINOMIMETIC AGENT; NATURAL PRODUCT; NUDIFLOSIDE A; NUDIFLOSIDE D; OCTAHYDROINDOLE; OIDIODENDROLIDE DERIVATIVE; PACTAMYCIN; PEPTIDOMIMETIC AGENT; PHENYLACETIC ACID; RESERPINE; RIFAMYCIN; TERPENE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKYLATION; CYCLIZATION; FRAGMENTATION REACTION; OLEFINATION; PROTON TRANSPORT; REVIEW; STEREOCHEMISTRY; SYNTHESIS; VISUAL REFLEX;

AMIDES; AMINO ACIDS; BIOLOGICAL AGENTS; CYCLOPENTANES; GLYCOSIDES; HISTORY, 20TH CENTURY; HISTORY, 21ST CENTURY; INDOLES; MACROLIDES; OLIGOPEPTIDES; PYRANS; PYRROLES; STEREOISOMERISM; TERPENES;

EID: 84865216375     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300902m     Document Type: Review

References (233)

1. Hanessian, S.; Giroux, S.; Merner, B. L.; Design and Strategy in Organic Synthesis: From the Chiron Approach to Catalysis; Wiley-VCH: Weinheim, 2012.
2. Nicolaou, K. C.; Chen, J. S. Classics in Total Synthesis III: Further Targets, Strategies, Methods; Wiley-VCH, Weinheim, 2011.
3. Corey, E. J.; Kürti, L. Enantioselective Chemical Synthesis: Methods, Logic, and Practice; Direct Book Publishing: Dallas, 2010.
4. For a historical perspective, see: Nicolaou, K. C.; Montagnon, T. Molecules that Changed the World, Wiley-VCH: Weinheim, 2008.
5. Corey, E. J.; Kürti, L.; Czakó, B. Molecules and Medicine; Wiley: New York, 2007.
6. Hanessian, S. ChemMedChem 2006, 1, 1300
7. Hanessian, S.; Franco, J.; Larouche, B. Pure Appl. Chem. 1990, 62, 1887
8. Hanessian, S. Reflections on the Total Synthesis of Natural Products: Art, Craft, Logic, and the Chiron Approach Pure Appl. Chem. 1993, 65, 1189
9. Hanessian, S. Design and Implementation of Tactically Novel Strategies for Stereochemical Control Using the Chiron Approach Aldrichimica Acta 1989, 22, 3
10. Hanessian, S. Total Synthesis of Natural Products: The "Chiron Approach"; Pergamon: Oxford, 1984.
11. Gawley, R.; Aubé, J. Principles of Asymmetric Synthesis, 2nd ed.; Pergamon: New York, 2012.
12. Fundamentals of Asymmetric Catalysis; Walsh, P. J.; Kozlowski, M., Eds.; University Science Books: Sausalito, 2008.
13. Catalysis of Organic Reactions; Schmidt, S. R., Ed.; CRC Press: Boca Raton, 2007.
14. 2 (1): Hanessian, S.; Lavallée, P. Can. J. Chem. 1977, 55, 562
15. Hanessian, S.; Lavallée, P. Can. J. Chem. 1981, 59, 870
16. Spectinomycin (2): Hanessian, S.; Roy, R. J. Am. Chem. Soc. 1979, 101, 5839
17. Hanessian, S.; Roy, R. J. Antibiot. 1979, 32, S-73
18. Azimic acid (3): Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391
19. Palitantin (4): Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623
20. Octosyl acid A (5): Hanessian, S.; Kloss, J. J. Am. Chem. Soc. 1986, 108, 2758
21. Hanessian, S.; Kloss, J.; Sugawara, T. ACS Symp. Ser. 1988, 64
22. Thienamycin (6): Hanessian, S.; Desilets, D.; Bennani, Y. J. Org. Chem. 1990, 55, 3098
23. Ajmalicine (7): Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947
24. Burseran (8): Hanessian, S.; Léger, R. Synlett 1992, 402
25. Tetrahydrolipstatin (9): Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768
26. Polyoximic acid (10): Hanessian, S.; Fu, J.-M.; Chiara, J.; DiFabio, R. Tetrahedron Lett. 1993, 34, 41557
27. Hanessian, S.; Fu, J.-M. Can. J. Chem. 2001, 79, 1812
28. Kainic acid (11): Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418
29. Pseudoannonacin A (12): Hanessian, S.; Abad-Grillo, T. J. Org. Chem. 1998, 63, 1049
30. Anthoplalone (13): Hanessian, S.; Cantin, L.-D.; Andreotti, D.; Gomtsyan, A. J. Org. Chem. 1999, 64, 4893
31. Azetidinecarboxylic acid (14): Hanessian, S.; Bernstein, S.; Yang, R.-Y.; Maguire, R. Bioorg. Med. Chem. Lett. 1999, 9, 1437
32. Dysinosin A (15): Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L. J. Am. Chem. Soc. 2002, 124, 13342
33. Malayamycin A (16): Hanessian, S.; Marcotte, S.; Machaalani, R.; Huang, G. Org. Lett. 2003, 5, 4277
34. Hanessian, S.; Marcotte, S.; Machaalani, R.; Huang, G.; Perron, J.; Loiseleur, O. Tetrahedron 2006, 62, 5201
35. Talaumidin (17): Hanessian, S.; Reddy, G. I. Synlett 2007, 475
36. Longicin (18): Hanessian, S.; Giroux, S.; Buffat, M. Org. Lett. 2005, 7, 3989
37. 1 (21): Hanessian, S.; Reddy, G. J.; Chahal, N. Org. Lett. 2006, 8, 5477
38. Aminoglycoside 66-40C (22): Hanessian, S.; Maianti, P. Chem. Commun. 2010, 46, 2013
39. Hanessian, S.; Maianti, P.; Ly, V. L.; Deschênes-Simard, B. Chem. Sci. 2012, 3, 249
40. ent- Cyclizidine (23): Hanessian, S.; Soma, U.; Dorich, S.; Deschênes-Simard, B. Org. Lett. 2011, 13, 1048
41. Lovell, F. M. J. Am. Chem. Soc. 1996, 88, 4510
42. Hanessian, S.; Kaltenbronn, J. S. J. Am. Chem. Soc. 1966, 88, 4509
43. Chabala, J. C.; Mrozik, H.; Tolman, R. L.; Eskola, P.; Lusi, A.; Peterson, L. H.; Woods, M. F.; Fisher, M. H.; Campbell, W. C.; Egerton, J. R.; Ostlind, D. A. J. Med. Chem. 1980, 23, 1134
44. Hanessian, S.; Ugolini, A.; Dubé, D.; Hodges, P. J.; André, C. J. Am. Chem. Soc. 1986, 108, 2276
45. Hanessian, S.; Ugolini, U.; Hodges, P.; Beaulieu, P.; Dubé, D.; André, C. Pure Appl. Chem. 1987, 59, 299
46. Hanessian, S.; Beaulieu, P.; Dubé, D. Tetrahedron Lett. 1986, 27, 5071
47. Hanessian, S.; Bacquet, C.; Lehong, N. Carbohydr. Res. 1980, 80, C17
48. See also: Hanessian, S. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.: Dekker: New York, 1996; Chapter 16, p 381.
49. Hanessian, S.; Lou, B. Chem. Rev. 2000, 100, 4443
50. Fraser-Reid, B.; Wolleb, H.; Faghih, R.; Barchi, J., Jr. J. Am. Chem. Soc. 1987, 109, 933
51. Pivichny, J. V.; Shim, J.-S.; Simmerman, L. A. J. Pharm. Sci. 1983, 733
52. Hanessian, S.; Dubé, D.; Hodges, P. J. J. Am. Chem. Soc. 1987, 109, 7063
53. Hanessian, S.; Chemla, P.; Tu, Y. Tetrahedron Lett. 1993, 34, 1407
54. Hanessian, S.; Chemla, P. Tetrahedron Lett. 1991, 32, 2719
55. Toeplitz, B. K.; Cohen, A. I.; Funke, P. T.; Parker, W. L.; Gougoutas, J. Z. J. Am. Chem. Soc. 1979, 101, 3344 and references cited therein
56. Hanessian, S.; Dehoff, B.; Cooke, N.; Sakito, N. J. Am. Chem. Soc. 1990, 112, 5276
57. Hanessian, S.; Murray, P. J. Tetrahedron 1987, 43, 5055
58. Hanessian, S.; Murray, P. J. J. Org. Chem. 1987, 52, 1171
59. Evans, D. A.; Nelson, J. V.; Taber, T. R. In Topics in Stereochemistry; Eliel, E.; Allinger, N., Eds.; Wiley-Interscience: New York, 1982; Vol. 13, p 1.
60. Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 3, p 1.
61. Evans, D. A.; Dow, R. L.; Shih, J. L.; Takacs, J. M.; Zahler, R. J. Am. Chem. Soc. 1990, 112, 5276
62. Lautens, M.; Colucci, J. J.; Hiebert, S.; Smith, N. D.; Bouchain, G. Org. Lett. 2002, 4, 1879
63. Hanessian, S.; Thavonekham, B.; Dehoff, B. J. Org. Chem. 1989, 54, 5831
64. Albers-Schönberg, G.; Joshua, M.; Lopez, M. B.; Hensens, O. D.; Springer, J. P.; Chen, J.; Ostrove, S.; Huffman, C. H.; Alberte, A. W.; Patchett, A. A. J. Antibiot. 1981, 34, 507
65. Rosen, T.; Heathcock, C. H. Tetrahedron 1986, 42, 4209
66. Hanessian, S.; Roy, P. J.; Petrini, M.; Hodges, P. J.; Di Fabio, R.; Garganico, G. J. Org. Chem. 1990, 55, 5766
67. Matsubara, S.; Takai, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1983, 56, 2029
68. Suzuki, M.; Takeda, H.; Noyori, R. J. Org. Chem. 1982, 47, 902
69. Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023
70. Stork, G. Pure Appl. Chem. 1989, 61, 439
71. Wender, D. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157
72. Martin, S. F.; Rueger, H.; Williamson, S. A.; Grzejszak, S. J. Am. Chem. Soc. 1987, 109, 6124
73. For a review, see: Chen, F.-E.; Huang, J. Chem. Rev. 2005, 105, 4671
74. Hanessian, S.; Pan, J.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem. 1997, 62, 465
75. Hanessian, S.; Di Fabio, R.; Marcoux, J.-F.; Prud'homme, M. J. Org. Chem. 1990, 55, 3436
76. Heno, Y.; Chimo, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564
77. Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741
78. Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140
79. Nagaoka, H.; Rutsch, W.; Schmid, G.; Iio, H.; Johnson, M. P.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7962
80. Iio, H.; Nagaoka, H.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7965
81. Hanessian, S.; Sumi, K. Synthesis 1991, 12, 1083
82. Hanessian, S.; Gai, Y.; Wang, W.; Olivier, E. J. Am. Chem. Soc. 1997, 119, 10034
83. Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919
84. Vishwa Karma, L. C.; Stringer, O. D.; Davis, F. A. Org. Synth. 1987, 66, 203
85. Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc. 1989, 111, 6524
86. Houk, K. N.; Moses, S. R.; Wu, Y.-D.; Rondan, N. G.; Jäger, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880
87. Stork, G.; Kahn, M. Tetrahedron Lett. 1983, 24, 3951
88. Hanessian, S.; Ma, J.; Wang, W. Tetrahedron Lett. 1999, 40, 4631
89. Hanessian, S.; Gai, Y.; Wang, W. G. Tetrahedron Lett. 1996, 37, 7473
90. Hanessian, S.; Ma, J.; Wang, W. Tetrahedron Lett. 1999, 40, 4631
91. Hanessian, S.; Gai, Y.; Wang, W. G. Tetrahedron Lett. 1996, 37, 7477
92. Werner, G.; Hagenmaier, H.; Drautz, H.; Baumgartner, A.; Zähner, H. J. Antibiot. 1984, 37, 110
93. Everett, J. R.; Baker, G. H.; Dorgau, R. J. J. J. Chem. Soc., Perkin Trans. 2 1990, 717
94. Corey, E. J.; Ponder, J. W. Tetrahedron Lett. 1984, 25, 4325
95. Hanessian, S.; Ma, J.; Wang, W.; Gai, Y. J. Am. Chem. Soc. 2001, 123, 10200
96. Evans, D. A.; Calter., M. A. Tetrahedron Lett. 1993, 34, 6871
97. Toshima, K.; Jyojima, T.; Yamaguchi, H.; Noguchi, Y.; Yoshida, T.; Murase, H.; Nakata, M.; Matsumara, S. J. Org. Chem. 1997, 62, 3271
98. Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed. 1999, 38, 1692
99. See also: Marshall, J. A.; Adams, N. A. Org. Lett. 2000, 2, 2897
100. Hanessian, S.; Meng, Q.; Olivier, E. Tetrahedron Lett. 1994, 35, 5393
101. Hanessian, S.; Tehim, A.; Meng, Q.; Granberg, K. Tetrahedron Lett. 1996, 37, 9001
102. Khosla, C. Chem. Rev. 1997, 97, 2577
103. Katz, L. Chem. Rev. 1997, 97, 2557
104. Berger, J.; Jampolsky, L. M.; Goldberg, M. W. Arch. Biochem. 1949, 22, 476
105. Keller-Schierlein, W. Helv. Chim. Acta 1967, 50, 731
106. Anderson, B. F.; Herlt, A. J.; Rickards, R. W.; Robertson, G. B. Aust. J. Chem. 1989, 42, 717
107. Hanessian, S.; Yang, Y.; Giroux, S.; Mascitti, V.; Ma, J.; Raeppel, F. J. Am. Chem. Soc. 2003, 125, 13784
108. Duffey, M. O.; Le Tiran, A.; Morken, J. D. J. Am. Chem. Soc. 2003, 125, 1458
109. Vong, B. G.; Kim, S. H.; Abraham, S.; Theodorakis, E. A. Angew, Chem. Int. Ed. 2004, 43, 3947
110. Nagamitsu, T.; Takano, D.; Fukuda, T.; Otoguro, K.; Kuwajima, I.; Harigaya, Y.; Õmura, S. Org. Lett. 2004, 6, 1865
111. Hanessian, S.; Giroux, S.; Mascitti, V. Proc. Nat. Acad. of Sci. U.S.A. 2004, 101, 11996
112. Ishiwata, H.; Nemoto, M.; Ojka, M.; Yamada, K. J. Org. Chem. 1994, 59, 4710
113. Ghosh, K. K.; Liu, C. Org. Lett. 2001, 3, 635
114. Hoffman, R. W. Angew. Chem., Int. Ed. 2000, 39, 2094
115. Hoffman, R. W.; Gottlich, R.; Schöpfer, U. Eur. J. Org. Chem. 2001, 1865
116. Kohno, J.; Nishio, M.; Sakurai, M.; Kawano, K.; Hajime, H.; Kameda, N.; Kishi, N.; Yamashita, T.; Okuda, J.; Komatsubara, S. Tetrahedron 1999, 55, 7771
117. Dale, J. J. Chem. Soc. 1963, 93
118. Dale, J. Angew, Chem. Int. Ed. 1966, 5, 1000
119. Celmer, W. D. Symposium on Antibiotics; Ste. Marguerite, Québec, Canada, Mar 1-3, 1971; Butterworths: London, 1971; pp 413-453.
120. Hanessian, S.; Chahal, N.; Giroux, S. J. Org. Chem. 2006, 71, 7403
121. Hanessian, S.; Giroux, S.; Mascitti, V. Synthesis 2006, 7, 1057
122. ter Horst, B.; Feringa, B. L.; Minaard, A. J. Chem. Commun. 2010, 46, 2535
123. Novak, T.; Tan, Z.; Liang, B.; Negishi, E.-I. J. Am. Chem. Soc. 2009, 127, 2838
124. Lopez, F.; Harutyunian, S. R.; Meetsma, A.; Minaard, A. J.; Feringa, B. L. Angew. Chem., Int. Ed. 2005, 44, 2752
125. Weise, C.; Pischl, M. C.; Pfaltz, A.; Schneider J. Org. Chem. 2012, 77, 1477
126. For a review, see: Ersmark, K.; DelValle, J. R.; Hanessian, S. Angew. Chem., Int. Ed. 2007, 46, 2
127. Carroll, A. R.; Pierens, G.; Fechner, G.; de Almeida Leone, P.; Ngo, A.; Simpson, M.; Hooper, J. N. A.; Boström, S.-L.; Musil, D.; Quinn, R. J. J. Am. Chem. Soc. 2002, 124, 13340
128. Hanessian, S.; Tremblay, M.; Petersen, J. F. W. J. Am. Chem. Soc. 2004, 126, 6064
129. Hanessian, S.; Del Valle, J. R.; Xue, Y.; Blomberg, N. J. Am. Chem. Soc. 2006, 128, 10491
130. Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817
131. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, J.; Heathcock, C. H., Eds.; Pergamon: New York, 1991, Vol. 2, p 1047.
132. Hanessian, S.; Margarita, R. Tetrahedron Lett. 1998, 39, 5887
133. Sun, P.; Weinreb, S. J. Org. Chem. 1997, 62, 8604
134. Hanessian, S.; Wang, X. Synlett 2009, 2803
135. Li, H.-T.; Jiang, X.-H.; Ye, Y.-H.; Fan, C.-Y.; Roncoff, T.; Goodman, M. Org. Lett. 1999, 1, 91
136. David, S.; Hanessian, S. Tetrahedron 1985, 41, 643
137. Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S.-H.; Safina, B. S. Angew. Chem., Int. Ed. 2005, 44, 1378
138. Hanessian, S.; Wang, X.; Ersmark, K.; Klegraf, E. Org. Lett. 2009, 11, 4232
139. Shin, H. J.; Matsuda, H.; Murakami, M.; Yamaguchi, K. J. Org. Chem. 1997, 62, 1810
140. Toyooka, N.; Nakazawa, A.; Himiyama, T.; Nemoto, H. Heterocycles 2003, 59, 75
141. see also: Valls, N.; Vallribera, M.; Font-Bardia, M.; Solans, X.; Bonjoch, J. Tetrahedron: Asymmetry 2003, 14, 1241
142. Hanessian, S.; Ersmark, K.; Wang, X; Del Valle, R. R.; Blomberg, N.; Xue, Y.; Fjellström, O. Bioorg. Med. Chem. Lett. 2007, 17, 3480
143. Hanessian, S.; Guillemette, S.; Ersmark, K. Chimia 2007, 61, 361
144. Banner, D. W.; D'Arcy, A.; Chene, C.; Winkler, F. K.; Guha, A.; Konigsberg, W. H.; Nemerson, Y.; Kirchhofer, D. Nature 1996, 380, 41
145. S. Hanessian, S.; Balaux, E.; Musil, D.; Olsson, L.-L.; Nilsson, I. Bioorg. Med. Chem. Lett. 2000, 10, 243
146. Hanessian, S.; Therrien, E.; Granberg, K.; Nilsson, I. Bioorg. Med. Chem. Lett. 2002, 12, 2907
147. Hanessian, S.; Sailes, H.; Therrien, E. Tetrahedron 2003, 59, 7047
148. Hanessian, S.; van Otterlo, W. A.L; Bayrakdarian, M.; Therrien, E.; Nilsson, I.; Petersen, J. Bioorg. Med. Chem. Lett. 2006, 16, 1032
149. Hanessian, S.; Simard, D.; Bayrakdarian, M.; Therrien, E.; Nilsson, I.; Fjellström, O. Bioorg. Med. Chem. Lett. 2008, 18, 1972
150. Hanessian, S.; Therrien, E.; van Otterlo, W.; Xue, Y.; Gustafsson, D.; Nilsson, I.; Fjellström, O. Bioorg. Med. Chem. Lett. 2009, 19, 5429
151. Hanessian, S. Pure Appl. Chem. 2009, 81, 1085
152. For example, see: The World Health Organization (WHO) Cardiovascular Disease (CVD) Global Strategy on Diet, Physical Activity and Health, WHO, 2003.
153. Hughes, B. Nat. Rev. Drug. Discov. 2010, 9, 903
154. Hanessian, S.; Tremblay, M.; Marzi, M.; Del Valle, J. R. J. Org. Chem. 2005, 70, 5070
155. S. Hanessian, S.; Tremblay, M. Org. Lett. 2004, 6, 4683
156. S. Hanessian, S.; Lu, P.-P.; Sancéau, J.-Y.; Chemla, P.; Prade, L.; Gohda, K.; Fonne-Pfister, R. Angew. Chem., Int. Ed. 1999, 38, 3159
157. Hanessian, S.; Huang, G.; Chenel, C.; Machaalani, R.; Loiseleur, O. J. Org. Chem. 2005, 70, 6721
158. Hanessian, S.; Ritson, D. J. J. Org. Chem. 2006, 71, 9807
159. Loiseleur, O.; Hermann, O.; Huang, S.; Machaalani, G.; Sellès, R.; Crowley, P.; Hanessian, P. S. Org. Proc. Res. Dev. 2006, 10, 518
160. Loiseleur, O.; Ritson, D.; Nina, M.; Crowley, P.; Wagner, T.; Hanessian, S. J. Org. Chem. 2007, 72, 6353
161. Barrero, A. F.; Quílez Del Moral, J. F.; Herrador, M. M. Stud. Nat. Prod. Chem 2003, 28, 3453
162. Banerjee, A. K.; Laya, M. S.; Moro, H. R.; Cabrera, E. L. Curr. Org. Chem. 2008, 12, 1050
163. John, M.; Krohn, K.; Flörke, U.; Aust, H.-J.; Draeger, S.; Schulz, B. J. Nat. Prod. 1999, 62, 1218
164. S. Hanessian, S.; Boyer, N.; Reddy, G. J.; Deschênes-Simard, B. Org. Lett. 2009, 11, 4640
165. Adrian, J. C., Jr.; Snapper, M. L. J. Org. Chem. 2003, 68, 2143
166. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533
167. Pearson, R. G. J. Chem. Educ. 1968, 45 (581) 643
168. See also: Ho, T.-L. Hard and Soft Acids and Bases Principle in Organic Chemistry; Academic: New York, 1977.
169. Ponpipom, M. M.; Hanessian, S. Carbohydr. Res. 1971, 18, 342
170. Hanessian, S.; Ponpipom, M. M.; Lavallée, P. Carbohyd. Res. 1972, 24, 45
171. Hanessian, S; Lavallée, P. J. Antibiot. (Japan) 1973, 25, 683
172. Hanessian, S.; Leblanc, Y.; Lavallée, P. Tetrahedron Lett. 1982, 23, 4411
173. Hanessian, S.; Bennani, Y. L.; Leblanc, Y. Heterocycles 1993, 35, 1411
174. For example, see: McMurray, J.; von Beroldingen Tetrahedron 1974, 30, 2027
175. Corey, E. J.; Kwiatkowsky, G. T. J. Am. Chem. Soc. 1968, 90, 6816
176. Corey, E. J.; Cane, D. E. J. Org. Chem. 1969, 34, 3053
177. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754
178. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161
179. Hanessian, S.; Beaudoin, S. Tetrahedron Lett. 1992, 33, 7655
180. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801
181. Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 159.
182. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327
183. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395
184. Hanessian, S.; Gomtsyan, A.; Payne, A.; Hervé, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032
185. Hanessian, S.; Gomtsyan, A.; Malek, N. J. Org. Chem. 2000, 65, 5623
186. Hanessian, S.; Gomtsyan, A. Tetrahedron Lett. 1994, 35, 7509
187. Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393
188. Hanessian, S.; Bennani, Y. L. Tetrahedron 1996, 52, 13847
189. Hanessian, S.; Bennani, Y. L.; Hervé, Y. Synlett 1993, 35
190. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272
191. Hanessian, S.; Cantin, L. D.; Roy, S.; Andreotti, D.; Gomtsyan, A. Tetrahedron Lett. 1997, 38, 1103
192. For example, see: Tanahashi, T.; Takenada, Y.; Nagakura, N.; Nishi, J. J. Nat. Prod. 1998, 62, 1311
193. Hanessian, S.; Mainetti, E.; Lecomte, F. Org. Lett. 2006, 8, 4047
194. Gerth, K.; Washausen, P.; Höfle, G.; Irschik, H.; Reichenbach, H. J. Antibiot. 1996, 49, 71
195. Hanessian, S.; Focken, T.; Oza, R. Org. Lett. 2010, 12, 3172
196. Connor, D. T.; Greenough, R. C.; von Strandtmann, M. J. Org. Chem. 1977, 42, 3664
197. Kende, A. S.; Mendoza, J. S.; Fuhii, Y. Tetrahedron 1993, 49, 8015
198. Berberich, S. M.; Cherney, R. J.; Colucci, J.; Courillon, C.; Geraci, L. S.; Kirkland, T. A.; Marx, M. A.; Schneider, M. F.; Martin, S. F. Tetrahedron 2003, 59, 6819
199. Lee, E.; Choi, S.; Kim, H.; Han, H. O.; Kim, Y. K.; Min, S. J.; Son, S. H.; Lim, S. M.; Jang, W. S. Angew. Chem., Int. Ed. 2002, 41, 176
200. Liu, P.; Jacobsen, E. N. J. A. Chem. Soc. 2001, 123, 10772
201. Hanessian, S.; Focken, T.; Mi, X.; Ritson, D.; Oza, R.; Chen, B.; Beaudegnies, R. J. Org. Chem. 2010, 75, 5601
202. Wiley, P. F.; Janke, H. K.; MacKellar, F.; Kelly, R. B.; Argoudelis, A. D. J. Org. Chem. 1970, 35, 1420
203. Duchamp, D. J. Abstracts J. Am. Crystal Assoc. Winter Meeting, Albuquerque, NM, 1972, April, p 23.
204. Weller, D. D.; Haber, A.; Rinehart, K. L., Jr. J. Antibiot. 1978, 31, 997
205. Brodersen, D. E.; Clemens, W. M.; Carter, A. P., Jr.; Morgan-Warren, R. J.; Wimberley, B. T.; Ramakrishnan, V. Cell 2000, 103, 1143
206. Hanessian, S.; Reddy Vakiti, R.; Dorich, S.; Banerjee, S.; Lecomte, F.; DelValle, J. R.; Zhang, J.; Deschênes-Simard, B. Angew. Chem., Int. Ed. 2011, 50, 3497
207. Hanessian, S.; Léger, S. J. Am. Chem. Soc. 1992, 114, 3115
208. For example, see: Kuivila, H. G.; Sommer, R. J. Am. Chem. Soc. 1967, 89, 5616
209. Hanessian, S.; Reinhold, U.; Gentile, G. Angew. Chem., Int. Ed. 1997, 36, 1881
210. Ondetti, M. A.; Cushman, D. W. J. Med. Chem. 1981, 24, 355
211. Cushman, D. W.; Ondetti, M. A. Prog. Med. Chem. 1980, 17, 41
212. Ondetti, M. A.; Rubin, B.; Cushman, D. W. Science 1977, 196, 441
213. Hanessian, S.; Reinhold, U.; Saulnier, M.; Claridge, S. Bioorg. Med. Chem. Lett. 1998, 8, 2123
214. Rohl, J. A.; Hamann, L. G. In Accounts of Drug Discovery; Barnish, J. C.; Carter, P. H.; Cheng, P. T. W.; Zahler, R.; Gwaltney, S. L., II; Stafford, J. A., Eds.; Royal Society of Chemistry: London, 2011; Chapter 1, p 1.
215. Annu. Rep. Med. Chem. 2005, 40, 156.
216. Enantioselective Organocatalysis: Reactions and Experimental Procedures; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, 2007.
217. Asymmetric Organocatalysis: From Biometric Concepts to Asymmetric Synthesis; Berkessel, A.; Gröger, H., Eds.; Wiley-VCH: Weinheim, 2005.
218. For a recent review, see: Marquez-Lopez, E.; Herrera, R. P.; Christmann, M. Nat. Prod. Rep. 2010, 27, 1138 and references cited therein
219. Hanessian, S.; Shao, Z.; Warrier, J. S. Org. Lett. 2006, 8, 4787
220. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975
221. Hanessian, S.; Govindan, S.; Warrier, J. S. Chirality 2005, 17, 540
222. Hanessian, S.; Shao, Z.; Betschart, C.; Rondeau, J.-M.; Neumann, U.; Tintelnot-Blomley, M. Bioorg. Med. Chem. Lett. 2010, 20, 1924
223. Hanessian, S.; Maji, D. K.; Govindan, S.; Matera, R.; Tintelnot-Blomley, M. J. Org. Chem. 2010, 75, 2861-2876
224. Fascinating Molecules in Organic Chemistry; Vögtle, F., Ed.; Wiley: New York, 1992.
225. Organic Chemistry: The Name Game; Nickon, A.; Silversmith, E. F., Eds.; Pergamon: New York, 1987.
226. Hanessian, S.; Mauduit, M. Angew. Chem., Int. Ed. 2001, 40, 3810
227. Hanessian, S.; Mauduit, M.; Demont, E.; Talbot, C. Tetrahedron 2002, 58, 1485
228. Hanessian, S.; Talbot, C.; Mauduit, M.; Parthasarathy, S.; Gone, J. R. Heterocycles 2006, 67, 205
229. Rozwadowska, M. D. Heterocycles 1994, 39, 903
230. Shamma, M.; Moniot, J. L.; Chinnasamy, P. Heterocycles 1977, 6, 399
231. Stevens, T. S.; Creighton, E. M.; Gordon, A. B.; Macnicol, M. J. Chem. Soc. 1928, 3193
232. Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon: New York, 1991; Vol. 3, p 913.
233. Hanessian, S.; Parthasarathy, S.; Mauduit, M.; Payza, K. J. Med. Chem. 2003, 46, 34