Unusual amino acids: Synthesis and introduction into naturally occurring peptides and biologically active analogues

Mini-Reviews in Medicinal Chemistry

Volumn 6, Issue 3, 2006, Pages 293-304

  Cardillo, G ^a   Gentilucci, L ^a   Tolomelli, A ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

substituted amino acids; substituted amino acids; Aziridines; Endomorphin; Lysobactin; Peptides; Peptidomimetics; Unusual amino acids

Indexed keywords

ALPHA AMINO ACID; AMINO ACID DERIVATIVE; AZIRIDINE DERIVATIVE; BETA AMINO ACID; DYNORPHIN; ENDOMORPHIN 1; ENDORPHIN; ENKEPHALIN; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; HYDROXYAMINO ACID; LYSOBACTIN; MACROLIDE; MORPHINE; MU OPIATE RECEPTOR AGONIST; OPIATE PEPTIDE; OXAZOLE DERIVATIVE; OXAZOLINE DERIVATIVE; PEPTIDE DERIVATIVE; PHENYLALANINE; THIAZOLE DERIVATIVE; TRYPTOPHAN; VANCOMYCIN;

AMINO ACID SYNTHESIS; ANALGESIC ACTIVITY; BIOAVAILABILITY; CHIRALITY; DRUG ACTIVITY; DRUG DEPENDENCE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOLERANCE; ENANTIOMER; HYDROLYSIS; IN VITRO STUDY; NONHUMAN; PEPTIDE SYNTHESIS; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; AMINO ACIDS; AZIRIDINES; BIOLOGICAL AVAILABILITY; DEPSIPEPTIDES; ENDORPHINS; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PEPTIDES; PROTEIN ENGINEERING; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 33646051966     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/138955706776073394     Document Type: Review

References (150)

1. (a) Freidinger, R. M. J. Med. Chem. 2003, 46, 5553-5566.
2. (b) Eguchi, M.; Kahn, M. Mini Rev. Med. Chem. 2002, 2, 447-462.
3. (c) Glenn, M. P.; Fairlie, D. P. Mini-Rev. Med. Chem. 2002, 2, 433-445.
4. (d) Goodmann, M.; Zapf, C.; Rew, Y. Biolpolymers 2001, 60, 229-245.
5. Chorev, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266-273.
6. (a) Cardillo, G.; Tolomelli, A.; Tomasini, C. Eur. J. Org. Chem. 1999, 155-161.
7. (b) Grandel, R.; Kazmaier, U. Eur. J. Org. Chem. 1998, 409-417.
8. (c) Belokon, Y: N.; Kochetkov, K. A.; Churkina,, T. D.; Ikonnikov, N. S.; Chesnokov, A.A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymm., 1998, 9, 851-857.
9. (d) Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
10. (e) Chinchilla, R.; Falvello, L.; Galindo, N.; Najera, C. Angew. Chem. Int. Ed. Engl. 1997, 36, 995-997.
11. (a) Alonso, E.; del Pozo, C.; Gonzalez, J. Synlett 2002, 69-72.
12. (b) Steer, D.; Lew, R. A.; Perlmutter, P.; Smith, A. I.; Aguilar, M.-I. Curr. Med. Chem. 2002, 9, 811-822.
13. (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
14. (b) Park, K.-H.; Kurth, M. J. Tetrahedron 2002, 58, 8629-8659.
15. (a) Li, P.; Roller, P. P.; Xu, J. Curr. Org. Chem. 2002, 6, 411-440.
16. (b) Fairlie, D. P.; Abbenante, G.; March, D. R. Curr. Med. Chem. 1995, 2, 654-686.
17. (a) Pattenden, G. Angew. Chem. Int. Ed. Engl. 1993, 32, 1-23.
18. (b) Wipf, P.; Venkatraman, S. Synlett 1997, 1-10.
19. (c) Wipf, P. Chem. Rev. 1995, 95, 2115-2134.
20. For an extensive study on β-amino acids see: Juaristi, E. Enantioselective Synthesis of β-amino acids, Wiley-VCH:New York, 1997.
21. (a) Drey, C. N. C. In Chemistry and Biochemistry of the Amino Acids, Barnett G. C. Ed.; Chapmann and Hall: London, 1985; p. 25-54.
22. (b) Drey, C. N. C. In Chemistry and Biochemistry of the Amino Acids, Peptides and Proteins, Weinstein, B. Ed.; Marcel Dekker: New York, 1977; Vol. 4, pp. 241-299.
23. (c) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3-11.
24. (a) North, M. J. Pept. Sci. 2000, 6, 301-313.
25. (b) Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206-6212.
26. (c) Abele, S.; Vogtli, K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1539-1558.
27. (a) Davies, S. G.; Fenwick, D. R.; Ichihara, O. Tetrahedron: Asymmetry 1997, 8, 3387-3391.
28. (b) Davies, S. G.; Diez, D.; Dominguez, S. H.; Garrido, N. M.; Kruchinin, D.; Price, P. D.; Smith, A. D. Org. Biomol. Chem. 2005, 3, 1284-1301.
29. (c) Beddow, J. E.; Davies, S. G.; Smith, A. D.; Russell, A. J. Chem. Commun. 2004, 23, 2778-2779.
30. (a) Davies, F. A.; Reddy, R. E. Tetrahedron: Asymmetry 1994, 5, 955-960.
31. (b) Davies, F. A.; Han, W.; Murphy, C. K. J. Org. Chem. 1993, 58, 4890-4896.
32. Cardillo, G.; Tomasini, C. in Enantioselective Synthesis of β-amino acids, Juaristi E. Ed.; Wiley-VCH: New York, 1997; pp. 211-248.
33. Cardillo, G.; Tolomelli, A.; Tomasini, C. J. Org. Chem. 1996, 61, 8651-8654.
34. Baldaro, E.; Fuganti, C.; Servi, S.; Tagliani, A.; Terreni, M. (Servi, S. Ed.) NATO ASI Ser., Ser. C 1992, 381, 175-188.
35. (a) Rossi, D.; Lucente, G.; Romeo, A. Experientia 1977, 1557-1559.
36. (b) Soloshonok, V. A.; Svedas, V. K.; Kukhar, V. P.; Kirilenko, A. G.; Rybakova, A. V.; Solodenko, V. A.; Fokina, N. A.; Kogut, O. V.; Galaev, I. Y.; Kozlova, E. V.; Shishkina, I. P.; Galushko, S. V. Synlett 1993, 339-341.
37. (a) Seebach, D.; Estermann, H. Tetrahedron Lett. 1987, 28, 3103-3106.
38. (b) Seebach, D.; Estermann, H. Helv. Chim. Acta 1988, 71, 1824-1839.
39. Taxol is a trademark of Bristol-Myers Squibb Co. For some references, see: (a) Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160-167.
40. (b) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44.
41. (c) Nicolaou, K. C.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1995, 34, 2079-2090.
42. (a) Ojima, I.; Lin, S.; Slater, J. C.; Wang, T.; Pera, P.; Bernacki, R. J.; Ferlini, C.; Scambia, G. Bioorg. Med. Chem. 2000,8, 1619-1628.
43. (b) Ojima, I. ChemBioChem 2004, 5, 628-635.
44. Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. J. Org. Chem. 1998, 63, 2351-2353.
45. Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Synlett 1999, 1727-1730.
46. (a) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498.
47. (b) Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666.
48. (c) Denis, J.- N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S., Greene, A. E. J. Chem. Soc. Perkin Trans. 11995, 1811-1815.
49. (a) Sewald, N. Amino Acids 1996, 11, 397-408.
50. (b) Yamamoto, Y.; Asao, N.; Tsukada, N. Adv. Asymm. Synth. 1998, 3, 1-37.
51. Bunnage, M. E.; Davies, S. G.; Goodwin, C. J.; Walters, I. A. S. Tetrahedron: Asymm. 1994, 5, 35-6.
52. (a) Etxebarria, J.; Vicario, J. L.; Badia, D.; Carrillo, L. J. Org. Chem. 2004, 69, 2588-2590.
53. (b) Podlech, J. Synth. Comm. 2000, 30, 1779-1786.
54. (c) Sibi, M. P.; Ji, J.; Sausker, J. B.; Jasperse, C. P. J. Am. Chem. Soc. 1999, 121, 7517-7526.
55. (d) Davies, S. G.; Sanganee, H. J.; Szolcsanyi, P. Tetrahedron 1999, 55, 3337-3354.
56. (e) Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J. F. Tetrahedron Lett. 1988, 29, 4411-4414.
57. (a) Li, K.; Cheng, X.; Hii, K. K. Eur. J. Org. Chem. 2004, 5, 959-964.
58. (b) Palomo, C.; Oiarbide, M.; Halder, R.; Kelso, M.; Gomez-Bengoa, E.; Garcia, J. M. J. Am. Chem. Soc. 2004,126, 9188-9189.
59. (c) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443.
60. (d) Sibi, M. P.; Assoc, Y. J. Am. Chem. Soc. 2001, 123, 9708-9709.
61. Roder, H.; Helmchen, G.; Peters, E. M.; Peters, K.; Von Schnering, H. G. Angew. Chem., 1984, 96, 895-896.
62. (a) Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trerè, A. J. Org. Chem. 1993, 58, 5615-5619.
63. (b) Bongini, A.; Cardillo, G.; Mingardi, A.; Tomasini, C. Tetrahedron: Asymmetry 1996, 7, 1457-1466.
64. (c) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Org. Lett. 2001, 3, 1165-1167.
65. (a) Zadina, J. E.; Hackler, L.; Ge, L. J.; Kastin, A. J. Nature 1997, 386, 499-502.
66. (b) Zadina, J. E.; Martin-Schild, S.; Gerall, A. A.; Kastin, A. J.; Hackler, L.; Ge, L. J.; Zhang, X. Ann. N. Y. Acad. Sci. 1999, 897, 136-144.
67. (a) Przewlocki, R.; Labuz, D.; Mika, J.; Przewlocka, B.; Tomboly, Cs.; Toth, G. Ann. N. Y. Acad. Sci. 1999, 897, 154-164.
68. (b) Przewlocki, R.; Przewlocka, B. Eur. J. Pharmacol. 2001, 429, 79-91.
69. (c) Vaccarino, A. L.; Kastin, A. J. Peptides 2001, 22, 2257-2328.
70. (d) McLay, R. N.; Pan, W.; Kastin, A. J. Peptides 2001, 22, 2181-2255.
71. (e) Drolet, G.; Dumont, E. C.; Gosselin, I.; Kinkead, R.; Laforest, S.; Trottier, J. F. Prog. Neuropsychopharmacol. Biol. Psychiatry 2001, 25, 729-741.
72. Corbett, A. D.; Paterson, S. J.; Kosterlitz, H. W. Handb. Exp. Pharmacol. 1993,104/I(Opioids I), 645-679.
73. (a) Pogozbeva, I. D.; Lomize, A. L.; Mosberg, H. I. Biophys. J. 1998, 75, 612-634.
74. (b) Palczewski, K.; Kumasaka, T.; Hori, T.; Behnke, C. A.; Motoshima, H.; Fox, B. A.; Le Trong, I.; Teller, D. C.; Okada, T.; Stenkamp, R. E.; Yamamoto, M.; Miyano, M. Science 2000, 289, 739-745.
75. (c) Marshall, G. R. Biopolymers 2001, 60, 246-277.
76. (a) Wilson, A. M.; Soignier, R. D.; Zadina, J. E.; Kastin, A. J.; Nores, W. L.; Olson, R. D.; Olson, G. A. Peptides 2000, 21, 1871-1874.
77. (b) Czapla, M. A.; Gozal, D.; Alea, O. A.; Beckerman, R. C.; Zadina, J. E. Am. J. Resp. Crit. Care Med. 2000, 162, 994-999.
78. Sugimoto-Watanabe, A.; Kubota, K.; Fujibayashi, K.; Saito, K. Jpn. J. Pharmacol., 1999, 81, 264-270.
79. (a) Subramanian, G.; Paterlini, M. G.; Portoghese, P. S.; Ferguson, D. M. J. Med. Chem. 2000, 43, 381-391.
80. (b) Subramanian, G.; Paterlini, M. G.; Larson, D. L.; Portoghese, P. S.; Ferguson, D. M. J. Med. Chem. 1998, 41, 4777-4789.
81. (c) Mosberg, H. I.; Fowler, C. B. J. Pept. Res. 2002, 60, 329-335.
82. Cardillo, G:, Gentilucci, L.; Melchiorre, P.; Spampinato, S. Bioorg. Med. Chem. Lett. 2000, 10, 2755-2758.
83. (a) Klein, S. I.; Czekaj, M.; Molino, B. F.; Bruce, F.; Chu, V. Bioorg. Med. Chem. Lett. 1997, 7, 1773-1778
84. (b) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med Chem. 1991, 34, 717-725.
85. (c) Galynker, I.; Still, W. C. Tetrahedron Lett. 1982, 43, 4461-4464.
86. Shiller, P. W. In Opioids 1, Hertz, A. Ed.; Springler-Verlag: Berlin, 1993; pp. 681-710.
87. Cardillo, G.; Gentilucci, L.; Qasem, A. R.; Sgarzi, F.; Spampinato, S. J. Med. Chem. 2002, 45, 2571-2578.
88. (a) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D. Helv. Chim. Acta 1996, 79, 2043-2065.
89. (b) Katzenellenbogen, J. A., Sugano, Y. Bioorg. Med. Chem. Lett. 1996, 6, 361-366.
90. Frackenphol, J.; Arvidsson, P. I.; Schreiber, J. V.; Seebach, D. ChemBioChem 2001, 2, 445-455.
91. (a) Harrison, C.; McNulty, S.; Smart, D.; Rowbotham, D. J.; Grandy, D. K.; Devi, L. A.; Lambert, D. G. Br. J. Pharmacol. 1999, 128, 472-478.
92. (b) Toll, L. J Pharm. Exp. Ther. 1995, 273, 721-727.
93. Spampinato, S.; Qasem, A. R.; Calienni, M., Murari, G.; Gentilucci, L.; Tolomelli, A.; Cardillo, G. Eur. J. Pharm. 2003, 469, 89-95.
94. Unger, V. M.; Hargrave, P. A.; Baldwin, J. M.; Schertler, G. F. Nature 1997, 389, 203-206.
95. (a) Fiori, S.; Renner, C.; Cramer, J.; Pegoraro, S.; Moroder, L. J. Mol. Biol. 1999, 291, 163-175.
96. (b) Hruby, V. J.; Agnes, R. S. Biopolymers 1999, 51, 391-410.
97. (c) Kazmierski, W. M.; Ferguson, R. D.; Lipkowski, A. W.; Hruby, V. J. Int. J. Pept. Protein Res. 1995, 46, 265-278.
98. (d) Janecka, A.; Fichna, J.; Mirowski, M.; Janecki, T. Min Rev. Med. Chem. 2002,2, 565-572.
99. (e) Podlogar, B. L.; Paterlini, M. G.; Ferguson, D. M.; Leo, G. C.; Demeter, D. A.; Brown, F. K.; Reitz, A. B. FEBS Left. 1998, 439,13-20.
100. (f) In, Y.; Minoura, K.; Ohishi, H.; Minakata, H.; Kamigauchi, M.; Sugiura, M.; Ishida, T. J. Pept. Res. 2001, 58, 399-412.
101. (a) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Qasem, A. R.; Spampinato, S.; Calienni, M. Org. Biomol. Chem. 2003,1, 3010-3014.
102. (b) Leitgeb B, Szekeres A, Toth G. J Pept Res. 2003, 62, 145-157.
103. Eguchi, M.; Shen, R. Y.; Shea, J. P.; Lee, M. S.; Kahn, M. J. Med. Chem. 2002, 45, 1395-1398.
104. For reviews on aziridine synthesis, see: (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
105. (b) Atkinson, R. S. Tetrahedron 1999, 55, 1519-1559.
106. (c) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693-1715.
107. (d) Kemp, J. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 7, Chapter 3.5.
108. (e) Antilla, J. C.; Wulff, W. D. Angew. Chem. Int. Ed. Engl. 2000,39, 4518-4521.
109. (f) Cardillo, G.; Gentilucci, L.; Tolomelli, A. Aldrichimica Acta 2003, 36, 39-50. For reviews on the reactions of aziridines, see:
110. (g) McCoull, W.; Davis, F. A. Synthesis 2000, 10, 1347-1365.
111. (h) Kulkarni, Y. S. Aldrichimica Acta 1999, 32, 18-27.
112. (i) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, U. K., 1991; Vol. 4, Chapter 4.9.
113. (l) Righi, G.; Bonini, C. Targets in Heterocycl. Syst. 2000, 4, 139-165.
114. (l) Lee, W. K.; Ha, H.-J. Aldrichimica Acta 2003, 36, 57-63.
115. (a) Hori, K.; Nishiguchi, T.; Nabeya, A. J. Org. Chem. 1997, 62, 3081-3088.
116. (b) Ferraris, D.; Drury, W. J., III; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568-4569.
117. (a) Cardillo, G.; Casolari, S.; Gentilucci, L.; Tomasini, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1848-1849.
118. (b) Bongini, A.; Cardillo, G.; Gentilucci, L.; Tomasini, C. J. Org. Chem. 1997, 62, 9148-9153.
119. Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Tetrahedron Lett. 1997, 39, 6953-6956.
120. Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron 2001, 57, 2807-2812.
121. Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Synlett 2000, 9, 1309-1311.
122. (a) Cardillo, G.; Gentilucci, L.; Tolomelli, A. Tetrahedron Letters, 1999, 40, 8261-8264.
123. (b) Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. J. Org. Chem., 1998, 63, 3458-3462.
124. (c) Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron: Asymm., 2001, 12, 563-569.
125. Cardillo, G.; Gentilucci, L.; Tolomelli, A. Chem. Commun. 1999, 167-168.
126. (a) Haberhauer, G.; Rominger, F. Eur. J. Org. 2003, 3209-3219.
127. (b) Wipf, P.; Fricht, P. C.; Geib, S. J.; Sefler, A. M. J. Am. Chem. Soc. 1998, 120, 4105-4112.
128. (c) Bertram, A.; Blake, A. J.; Gonzalez-Lopez de Turiso, F.; Hannam, J. S.; Joliffe, K. A.; Pattenden, G.; Skae, M. Tetrahedron 2003, 59, 6979-6990.
129. (a) Hambley, T. W.; Hawkins, C. J.; Lavin, M. F.; Brenk, A. Watters, D. J. Tetrahedron 1992, 48, 341-348.
130. (b) Prinsep, M.R.; Moore, R. E.; Levine, I. A.; Patterson, G. M. L. J. Nat. Prid. 1992, 55, 140-142.
131. (a) Hamamoto, Y.; Endo, M.; Nakagawa, M.; Nakanishi, T.; Mizukawa, K. J. Chem. Soc. Chem. Commun. 1983, 323-324.
132. (b) Hamada, Y.; Kato, S.; Shioiri, T. Tetrahedron Lett. 1985, 26, 3223-3226.
133. Van der Brenk, A. L.; Tyndall, J. D. A.; Cusack, R. M.; Jones, A.; Fairlie, D. P., Gahan, L. R.; hanson, G. R. J. Inorg. Biochem. 2004, 98, 1857-1866.
134. Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Eur. J. Org. Chem. 2000, 2489-2494.
135. (a) O'Sullivan, J.; McCullough, J. E.; Tymiak, A. A.; Kirsch, D. R.; Trejo, W. H.; Principe, P. A. J. Antibiot. 1988,41, 1740-1744.
136. (b) Tymiak, A. A.; McCormick, T. J.; Unger, S. E. J. Org. Chem. 1989, 54, 1149-1157.
137. (c) Blackburn, R. K.; Van Breemen, R. B. Drug Metab. Dispos. 1993, 21, 573-579.
138. (a) Shoji, J.; Hinoo, H.; Matsumoto, K.; Hattori, T.; Yoshida, T.; Matsuura, S.; Kondo, E. J. Antibiot. 1988, 41, 713-718.
139. (b) Kato, T.; Hinoo, H.; Terui, Y.; Kikuchi, J.; Shoji, J. J. Antibiot. 1988, 41, 719-725.
140. (a) Hiramatsu, K. Lancet Infect. Dis. 2001, 1, 147.
141. (b) Sussmuth, R. D. ChemBioChem 2002, 3, 295-298.
142. (c) Nicolaou, K. C.; Boddy, C. N. C.; Braese, S.; Winssinger, N. Angew. Chem. Int. Ed. Engl. 1999, 38, 2097-2152.
143. Maki, H.; Miura, K.; Yamano, Y. Antimicrob. Agents Chemother. 2001, 45, 1823-1827.
144. Armaroli, S.; Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Org. Lett. 2000, 2, 1105-1107.
145. (a) Casiraghi, G.; Zanardi, F.; Rassu, G.; Spann, P. Chem. Rev. 1995, 95, 1677-1716.
146. (b) Sewald. N.; Hiller, K. D.; Körner, M.; Findeisen, M. J. Org. Chem. 1998, 63, 7263-7274.
147. (c) Pan, S.; Amankulor, N. M.; Zbao, K. Tetrahedron 1998, 54, 65 87-6604.
148. Bols, M.; Lundt, I. Acta Chem. Scand 1991, 45, 280-284.
149. (a) Cardillo, G.; Gentilucci, L.; Pericot Mohr, G. Eur. J. Org. Chem. 2001, 3545-3551.
150. (b) Cardillo, G.; Gentilucci, L.; De Matteis, V. J. Org. Chem. 2002, 67, 5957-5962.