Biomimetic Synthesis of Ornithine/Arginine and Lysine-Derived Alkaloids: Selected Examples

Biomimetic Organic Synthesis

Volumn 1, Issue , 2011, Pages 1-59

  Poupon, Erwan ^a   Salame, Rim ^a   Yan, Lok Hang ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Biomimetic synthesis; Lysine derived alkaloids; Ornithine arginine derived alkaloids; Pelletierine based metabolism

Indexed keywords

EID: 84885496199     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527634606.ch1     Document Type: Chapter

References (181)

1. Wu, G. (2009) Amino Acids, 37, 1-17.
2. Wu, G., Bazer, F.W., Davis, T.A., Kim, S.W., Li, P., Rhoads, J.M., Satterfield, M.C., Smith, S.B., Spencer, T.E., and Yin, Y. (2009) Amino Acids, 37, 153-168.
3. Torruella, G., Suga, H., Riutort, M., Pereto, J., and Ruiz-Trillo, I. (2009) J. Mol. Evol., 69, 240-248 and references cited therein.
4. Azevedo, R.A. and Lea, P.J. (2001) Amino Acids, 20, 261-279.
5. Dewick, P.M. (2009) Medicinal Natural Product: A Biosynthetic Approach, 3rd edn. John Wiley & Sons, Ltd, Chichester.
6. Hashimoto, T., Yukimune, Y., and Yamada, Y. (1989) Planta, 178, 131-137.
7. Biastoff, S., Brandt, W., and Drager, B. (2009) Phytochemistry, 70, 1708-1718.
8. Brown, A.M., Robins, D.J., Witte, L., and Wink, M. (1991) Plant Physiol. (Life Sci. Adv.), 10, 179-185.
9. Tanner, J.J. (2008) Amino Acids, 35, 719-730
10. Verbruggen, N. and Hermans, C. (2008) Amino Acids, 35, 753-759
11. Vidal, J. (2009) in Amino Acids, Peptides and Proteins in Organic Chemistry, vol. 2 (ed. A.B. Hughes), Wiley-VCHVerlag GmbH, Weinheim, pp. 35-92
12. Ciufolini, M.A. and Xi, N. (1998) Chem. Soc. Rev., 27, 437-446.
13. Guggisberg, A. and Hesse, M. (1983) in The Alkaloids, Chemistry and Pharmacology, vol. 22 (ed. A. Brossi), Academic Press Inc., New York, pp. 85-188
14. Schafer, A., Benz, H., Fiedler, W., Guggisberg, A., Bienz, S., and Hesse, M. (1994) in The Alkaloids, Chemistry and Pharmacology, vol. 45 (eds A. Brossi and G.A. Cordell), Academic Press Inc., San Diego, pp. 1-125
15. Bienz, S., Detterbeck, R., Ensch, C., Guggisberg, A., Hausermann, U., Meisterhans, C., Wendt, B., Werner, C., and Hesse, M. (2002) in The Alkaloids, Chemistry and Pharmacology, vol. 58 (ed. G. Cordell), Academic Press Inc., San Diego, pp. 83-338
16. Bienz, S., Bisseger, P., Guggisberg, A., and Hesse, M. (2005) Nat. Prod. Rep., 22, 647-648.
17. Seiler, N. (2004) Amino Acids, 26, 217-233.
18. Dimitrov, V., Geneste, H., Guggisberg, A., and Hesse, M. (2001) Helv. Chim. Acta, 84, 2108-2118.
19. Struve, C. and Christophersen, C. (2003) Heterocycles, 60, 1907-1914.
20. Houen, G., Struve, C., Søndergaard, R., Friis, T., Anthoni, U., Nielsen, P.H., Christophersen, C., Petersen, B.O., and Duus, J.Ø. (2005) Bioorg. Med. Chem., 13, 3783-3796.
21. Crocker, S.J., Loeffler, R.S.T., Smith, T.A. and Sessions, R.B. (1983) Tetrahedron Lett., 24, 1559-1560 and references cited therein.
22. Feth, F., Wray, F., and Wagner, K.G. (1985) Phytochemistry, 24, 1653-1655.
23. Wei, X., Sumithran, S.P., Deaciuc, A.G., Burton, H.R., Bush, L.P., Dwoskin, L.P., and Crooks, P.A. (2005) Life Sci., 78, 495-505.
24. Leete, E., Kim, S.H., and Rana, J. (1988) Phytochemistry, 27, 401-406
25. Leonard, N.J. and Cook, A.G. (1959) J. Am. Chem. Soc., 81, 5627-5631.
26. Swan, G.A. and Wilcock, J.D. (1974) J. Chem. Soc. Perkin Trans. 1, 885-891.
27. Franck, B. and Randau, D. (1966) Angew. Chem. Int. Ed. Engl., 5, 131.
28. Schopf, C., Komzak, A., Braun, F., Jacobi, E., Bormuth, M.-L., Bullnheimer, M., and Hagel, I. (1948) Justus Liebigs Ann. Chem., 559, 1-42.
29. Kessler, H., Mohrle, H., and Zimmermann, G. (1977) J. Org. Chem., 42, 66-72.
30. Schopf, C., Braun, F., Koop, H., Werner, G., Bressler, H., Neisius, K., and Schmadel, E. (1962) Justus Liebigs Ann. Chem., 658, 156-168.
31. Schopf, C., Braun, F., and Komzak, A. (1956) Chem. Ber., 89, 1821-1833.
32. Schopf, C., Arm, H., and Krimm, H. (1951) Chem. Ber., 84, 690-699
33. Schopf, C. and Otte, K. (1956) Chem. Ber., 89, 335-340.
34. El-Shazly, A.M., Dora, G., and Wink, M. (2005) Pharmazie, 60, 949-952.
35. Salame, R., Gravel, E., Retailleau, P., and Poupon, E. (2010) Org. Biomol. Chem., 8, 2522-2528.
36. Tashima, T., Imai, M., Kuroda, Y., Yagi, S., and Nakagawa, T. (1991) J. Org. Chem., 56, 694-697.
37. Francois, D., Lallemand, M.-C., Selkti, M., Tomas, A., Kunesch, N., and Husson, H.-P. (1998) Angew. Chem. Int. Ed., 37, 104-105.
38. Roulland, E., Cecchin, F., and Husson, H.-P. (2005) J. Org. Chem., 70, 4474-4477
39. Husson, H.-P. and Royer, J. (1999) Chem. Soc. Rev., 28, 383-394.
40. Zacharius, R.M., Thompson, J.F., and Steward, F.C. (1952) J. Am. Chem. Soc., 74, 2949.
41. He, M. (2006) J. Ind. Microbiol. Biotechnol., 33, 401-407
42. Broquist, H.P. (1991) Annu. Rev. Nutr., 11, 435-448.
43. Gatto, G.J., Boyne, M.T., Kelleher, N.L., and Walsh, C.T. (2006) J. Am. Chem. Soc., 128, 3838-3847 and references cited therein.
44. Zabriskie, T.M., Kelly, W.L., and Liang, X. (1997) J. Am. Chem. Soc., 119, 6446-6447.
45. Naranjo, L., Martin de Valmaseda, E., Bañuelos, O., Lopez, P., Riaño, J., Casqueiro, J., and Martin, J.F. (2001) J. Bacteriol, 183, 7165-7172.
46. Matsumoto, S., Yamamoto, S., Sai, K., Maruo, K., Adachi, M., Saitoh, M., Nishizaki, T. (2003) Brain Res., 980, 179-184 and references cited therein.
47. Lemire, A. and Charette, A.B. (2010) J. Org. Chem., 75, 2077-2080 and references cited therein for previous work.
48. Kadouri-Puchot, C. and Comesse, S. (2005) Amino Acids, 29, 101-130.
49. Aketa, K.-I., Terashima, S., and Yamada, S.-I. (1976) Chem. Pharm. Bull., 24, 621-631.
50. Rossen, K., Kolarovic, A., Baskakov, D., and Kiesel, M. (2004) Tetrahedron Lett., 45, 3023-3025.
51. Pal, B., Ikeda, S., Kominami, H., Kera, Y., and Ohtani, B. (2003) J. Catal., 217, 152-159
52. Ohtani, B., Tsuru, S., Nishimoto, S., Kagiya, T., and Izawa, K. (1990) J. Org. Chem., 55, 5551-5553.
53. Ober, D. and Kaltenegger, E. (2009) Phytochemistry, 70, 1687-1695
54. Robins, D.J. (1995) in The Alkaloids, Chemistry and Pharmacology vol. 46 (ed. G.A. Cordell), Academic Press Inc., San Diego, pp. 1-61.
55. Marson, C.M., Pink, J.H., Smith, C., Hursthouse, M.B., and Abdul Malik, K.M. (2000) Tetrahedron Lett., 41, 127-129.
56. Gribble, G.W. and Soll, R.M. (1981) J. Org. Chem., 46, 2433-2434
57. Gribble, G.W., Switzer, F.L., and Soll, R.M. (1988) J. Org. Chem. 53, 3164-3170.
58. Lamberton, J.A. (1973) in The Alkaloids, vol. 14 (ed. R.H.F. Manske), Academic Press Inc., New York, pp. 325-346 and references cited in Reference [54].
59. Onaka, T. (1971) Tetrahedron Lett., 12, 4395-4398.
60. Bick, I.R.C., Gunawardana, Y.A.G.P., and Lamberton, J.A. (1985) Tetrahedron, 41, 5627-5631.
61. Tufariello, J.J. and Ali, Sk.A. (1979) Tetrahedron Lett., 20, 4445-4448.
62. Chen, C.-K., Hortmann, A.G., and Marzabadi, M.R. (1988) J. Am. Chem. Soc., 110, 4829-4831.
63. Diker, K., El Biach, K., Doe de Maindreville, M., and Levy, J. (1997) J. Nat. Prod., 60, 791-793.
64. Carroll, A.R., Arumugan, G., Quinn, R.J., Redburn, J., Guymer, G., and Grimshaw, P. (2005) J. Org. Chem., 70, 1889-1892
65. Katavic, P.L., Venables, D.A., Forster, P.I., Guymer, G., and Carroll, A.R. (2006) J. Nat. Prod., 69, 1295-1299
66. Katavic, P.L., Venables, D.A., Rali, T., and Carroll, A.R. (2007) J. Nat. Prod., 70, 866-868.
67. Kurasaki, H., Okamoto, I., Morita, N., and Tamura, O. (2009) Org. Lett., 11, 1179-1181 and references cited therein.
68. Wu, J.-B., Cheng, Y.-D., Kuo, S.-C., Wu, T.-S., Iitaka, Y., Ebizuka, Y., and Sankawa, U. (1994) Chem. Pharm. Bull., 42, 2202-2204.
69. Twin, H., Wen, W.W.-H., Powell, D.A., Lough, A.J., and Batey, R.A. (2007) Tetrahedron Lett., 48, 1841-1844.
70. Snider, B.B. and Neubert, B.J. (2005) Org. Lett., 7, 2715-2718.
71. Baumgartner, B., Erdelmeier, C.A.J., Wright, A.D., Rali, T., and Sticher, O. (1990) Phytochemistry, 29, 3327-3330.
72. Datwyler, P., Ott-Longoni, R., Schopp, E., and Hesse, M. (1981) Helv. Chim. Acta, 64, 1959-1963.
73. Ott-Longoni, R., Viswanathan, N., and Hesse, M. (1980) Helv. Chim. Acta, 63, 2119-2129.
74. Tapiolas, D.M., Bowden, B.F., Abou-Mansour, E., Willis, R.H., Doyle, J.R., Muirhead, A.N., Liptrot, C., Llewellyn, L.E., Wolff, C.W.W., Wright, A.D., and Motti, C.A. (2009) J. Nat. Prod., 72, 1115-1120
75. Swersey, J.C., Ireland, C.M., Cornell, L.M., and Peterson, R.W. (1994) J. Nat. Prod., 57, 842-845.
76. Casapullo, A., Finamore, E., Minale, L., and Zollo, F. (1993) Tetrahedron Lett., 34, 6297-6300
77. Casapullo, A., Minale, L., Zollo, F., and Lavayre, J. (1994) J. Nat. Prod., 57, 1227-1233.
78. Snider, B.B., Song, F., and Foxman, B.M. (2000) J. Org. Chem., 65, 793-800.
79. Barykina, O.V. and Snider, B.B. (2010) Org. Lett., 12, 2664-2667.
80. Robinson, R.J. (1917) J. Chem. Soc., 111, 762-768.
81. Schopf, C. (1937) Angew. Chem., 50, 779-787.
82. Humphrey, A.J. and O'Hagan, D. (2001) Nat. Prod. Rep., 18, 494-502.
83. Jonsson, D., Molin, H., and Unden, A. (1998) Tetrahedron Lett., 39, 1059-1062.
84. Mikami, K. and Ohmura, H. (2002) Chem. Commun., 2626-2627.
85. Davis, F.A., Theddu, N., and Gaspari, P.M. (2009) Org. Lett., 11, 1647-1650.
86. Arend, M., Westermann, B., and Risch, N. (1998) Angew. Chem. Int. Ed., 37, 1044-1070.
87. Nicolaou, K.C. and Montagnon, T. (2008) Molecules That Changed the World, Wiley-VCH Verlag GmbH, Weinheim.
88. Nakano, H., Kosemura, S., Suzuki, T., Hirose, K., Kaji, R., and Sakai, M. (2009) Tetrahedron Lett., 50, 2003-2005.
89. Saito, K. and Murakoshi, I. (1995) in Studies in Natural Products Chemistry, vol. 15 (ed. A.-U. Rahman), Elsevier Science, Amsterdam, pp. 519-549
90. Ohmiya, S., Saito, K., and Murakoshi, I. (1995) in The Alkaloids, Chemistry and Pharmacology, vol. 47 (ed. G.A. Cordell), Academic Press Inc., San Diego, pp. 1-114
91. Sekine, T., Saito, K., Minami, K., Arai, N., Suzuki, H., Koike, Y., and Murakoshi, I. (1993) Yakugaku Zasshi, 113, 53-62.
92. Wanner, M.J. and Koomen, G.-J. (1996) J. Org. Chem., 61, 5581-5586.
93. Norcross, N.R., Melbardis, J.P., Ferris Solera, M., Sephton, M.A., Kilner, C., Zakharov, L.N., Astles, P.C., Warriner, S.L., and Blakemore, P.R. (2008) J. Org. Chem., 73, 7939-7951
94. Hermet, J.-P.R., McGrath, M.J., O'Brien, P., Porter, D.W., and Gilday, J. (2004) Chem. Commun., 1830-1831
95. Smith, B.T., Wendt, J.A., and Aube, J. (2002) Org. Lett., 4, 2577-2579
96. van Tamelen, E.E. and Foltz, R.L. (1969) J. Am. Chem. Soc., 91, 7372-7377.
97. Mure, M. and Klinman, J.P. (1995) J. Am. Chem. Soc., 117, 8698-9702
98. Mure, M. and Klinman, J.P. (1995) J. Am. Chem. Soc., 117, 8707-8718
99. Lee, Y. and Sayre, L.M. (1995) J. Am. Chem. Soc., 117, 11823-11828.
100. Largeron, M., Neudorffer, A., and Fleury, M.-B. (2003) Angew. Chem. Int. Ed., 42, 1026-1029.
101. Murakoshi, I., Kidoguchi, E., Haginiwa, J., Ohmiya, S., Higashiyama, K., and Otomasu, H. (1981) Phytochemistry, 20, 1407-1409
102. Frigerio, F., Haseler, C.A., and Gallagher, T. (2010) Synlett, 729-730.
103. Wanner, M.J. and Koomen, G.-J. (1994) in Studies in Natural Products Chemistry, vol. 14 (ed. A.-U. Rahman), Elsevier, Amsterdam, pp. 731-768
104. Wanner, M.J. and Koomen, G.J. (1994) Pure Appl. Chem., 66, 2239-2242
105. Wanner, M.J. and Koomen, G.J. (1996) Pure Appl. Chem., 68, 2051-2056
106. Wanner, M.J. and Koomen, G.J. (1997) J. Indian Chem. Soc., 74, 891-895; (e)
107. Wanner, M.J. and Koomen, G.J. (1997) Invited lecture presented at the International Conference on Biodiversity and Bioresources: Conservation and Utilization, Phuket, Thailand, November 23-27, 1997
108. http://old.iupac.org/symposia/proceedings/phuket97/wanner.html, accessed 26 August 2010
109. Wanner, M.J. and Koomen, G.-J. (1995) J. Org. Chem., 60, 5634-5637.
110. Gravel, E., Poupon, E., and Hocquemiller, R. (2005) Org. Lett., 7, 2497-2499.
111. Duan, J.-A., Williams, I.D., Che, C.-T., Zhou, R.-H., and Zhao, S.-X. (1999) Tetrahedron Lett., 40, 2593-2596.
112. Salame, R., Gravel, E., and Poupon, E. (2009) Org. Lett., 11, 1891-1894.
113. Putkonen, T., Tolvanen, A., Jokela, R., Caccamese, S., and Parrinello, N. (2003) Tetrahedron, 59, 8589-8595.
114. Gravel, E. and Poupon, E. (2010) Nat. Prod. Rep., 27, 32-56.
115. Wanner, M.J. and Koomen, G.-J. (1995) J. Org. Chem., 60, 5634-5637
116. Wanner, M.J. and Koomen, G.-J. (1994) J. Org. Chem., 59, 7479-7484.
117. Francois, D., Lallemand, M.-C., Selkti, M., Tomas, A., Kunesch, N., and Husson, H.-P. (1997) J. Org. Chem., 62, 8914-8916
118. Francois, D., Lallemand, M.C., Selkti, M., Tomas, A., Kunesch, N., and Husson, H.-P. (1998) Angew. Chem. Int. Ed., 37, 104-105.
119. Pham, V.C., Jossang, A., Sevenet, T., Nguyen, V.H., and Bodo, B. (2007) Tetrahedron, 63, 11244-11249
120. Pham, V.C., Jossang, A., Sevenet, T., Nguyen, V.H., and Bodo, B. (2007) J. Org. Chem., 72, 9826-9829.
121. Leonard, N.J. and Cook, A.G. (1959) J. Am. Chem. Soc., 81, 5627-5631
122. Leonard, N.J. and Hauck, F.P. Jr. (1957) J. Am. Chem. Soc., 79, 5279-5292.
123. Leonard, N.J. and Musker, K. (1959) J. Am. Chem. Soc., 81, 5631-5633.
124. Schildknecht, H., Krauss, D., Connert, J., Essenbreis, H., and Orfanides, N. (1975) Angew. Chem. Int. Ed. Engl., 14, 427
125. Schildknecht, H., Berger, D., Krauss, D., Connert, J., Gehlhaus, H., and Essenbreis, H. (1976) J. Chem. Ecol., 2, 1-11.
126. Enders, D., Tiebes, J., De Kimpe, N., Keppens, M., Stevens, C., Smagghe, G., and Betz, O. (1993) J. Org. Chem., 58, 4881-4884.
127. Poupon, E., Kunesch, N., and Husson, H.-P. (2000) Angew. Chem. Int. Ed., 39, 1493-1495.
128. Lusebrink, I., Dettner, K., and Seifert, K. (2008) J. Nat. Prod., 71, 743-745.
129. Tanret, C. (1878) C. R. Acad. Sci., 86, 1270-1272
130. Tanret, C. (1880) C. R. Acad. Sci., 90, 695-698.
131. Hess, K. and Eichel, A. (1917) Ber. Dtsch. Chem. Ges., 50, 1192-1199.
132. Kuwata, S. (1960) Bull. Chem. Soc. Jpn., 33, 1668-1672
133. Kuwata, S. (1960) Bull. Chem. Soc. Jpn., 33, 1672-1678.
134. Gilman, R.E. and Marion, L. (1961) Bull. Soc. Chim. Fr., 1993-1995 and references cited therein.
135. Drillien, G. and Viel, C. (1963) Bull. Soc. Chim. Fr., 2393-2340.
136. Beyerman, H.C., Maat, L., van Veen, A., Zweistra, A., and von Philipsborn, W. (1965) Rec. Trav. Chim. Pays-Bas, 84, 1367-1379
137. Craig, J.C., Lee, S.Y.C., and Roy, S.K. (1978) J. Org. Chem., 43, 347-349.
138. Gupta, R.N. and Spenser, I.D. (1969) Can. J. Chem., 47, 445-447
139. Hemscheidt, T. and Spenser, I.D. (1990) J. Am. Chem. Soc., 112, 6360-6363 and references cited therein.
140. Anet, E.F.L., Hughes, G.K., and Ritchie, E. (1949) Nature, 164, 501
141. Anet, E.F.L., Hughes, G.K., and Ritchie, E. (1950) Aust.J. Sci. Res. A, 3, 336-341
142. Schopf, C. (1949) Angew. Chem., 61, 31
143. Wisse, J.H., De Klonia, H., and Visser, B.J. (1964) Rec. Trav. Chim. Pays-Bas, 83, 1265-1272
144. Quick, J. and Oterson, R. (1976) Synthesis, 745-756.
145. Takahata, H., Kubota, M., Takahashi, S., and Momose, T. (1996) Tetrahedron: Asymmetry, 7, 3047-3054
146. Turcaud, S., Martens, T., Sierecki, E., Perard-Viret,J., and Royer, J. (2005) Tetrahedron Lett., 46, 5131-5134
147. Carlson, E.C., Rathbone, L.K., Yang, H., Collett, N.D., and Carter, R.G. (2008) J. Org. Chem., 73, 5155-5158.
148. Quick, J. and Meltz, C. (1979) J. Org. Chem., 44, 573-578 and references cited therein.
149. Cope, A.C., Dryden, H.L., Overberger, C.G., and D'Addieco, A.A. (1951) J. Am. Chem. Soc., 73, 3416-3418 and references cited therein.
150. Bates, R.W. and Sa-Ei, K. (2002) Tetrahedron, 58, 5957-5978.
151. Felpin, F.-X. and Lebreton, J. (2004) Tetrahedron, 60, 10127-10153.
152. Krishnan, S., Bagdanoff, J.T., Ebner, D.C., Ramtohul, Y.K., Tambar, U.K., and Stoltz, B.M. (2008) J. Am. Chem. Soc, 130, 13745-13754 and references cited therein for recent syntheses of Lobelia and Sedum alkaloids.
153. Ma, X. and Gang, D.R. (2004) Nat. Prod. Rep., 21, 752-772
154. Kobayashi, J. and Morita, H. (2005) in The Alkaloids, Chemistry and Biology, vol. 61 (ed. G.A. Cordell), Elsevier, San Diego, pp. 1-57
155. Hirasawa, Y., Kobayashi, J., and Morita, H. (2009) Heterocycles, 77, 679-729.
156. Hemscheidt, T. and Spenser, I.D. (1996) J. Am. Chem. Soc., 118, 1799-1800
157. Conroy, H. (1960) Tetrahedron Lett., 1, 34-37.
158. Wenkert, E., Chauncy, B., Dave, K.G., Jeffcoat, A.R., Schell, F.M., and Schenk, H.P. (1973) J. Am. Chem. Soc., 95, 8427-8436.
159. Scott, W.L. and Evans, D.A. (1972) J. Am. Chem. Soc., 94, 4779-4780.
160. Heathcock, C.H., Kleinman, E.F., and Binkley, E.S. (1982) J. Am. Chem. Soc., 104, 1054-1068.
161. Schumann, D., Muller, H.-J., and Naumann, A. (1982) Liebigs. Ann. Chem., 2057-2061.
162. Yang, Y.-R., Lai, Z.-W., Shen, L., Huang, J.-Z., Wu, X.-D., Yin, J.-L., and Wei, K. (2010) Org. Lett., 12, 3430-3433
163. Canham, S.M., France, D.J., and Overman, L.E. (2010) J. Am. Chem. Soc., 132, 7876-7877
164. Yuan, C., Chang, C.-T., Axelrod, A., and Siegel, D. (2010) J. Am. Chem. Soc., 132, 5924-5925
165. Fischer, D.F. and Sarpong, R. (2010) J. Am. Chem. Soc., 132, 5926-5927
166. Bisai, V. and Sarpong, R. (2010) Org. Lett., 12, 2551-2553
167. Chandra, A., Pigza, J.A., Han, J.-S., Mutnick, D., and Johnston, J.N. (2009) J. Am. Chem. Soc., 131, 3470-3471
168. Nishimura, T., Unni, A.K., Yokoshima, S. and Fukuyama, T. (2011) J. Am. Chem. Soc., 133, 418-419.
169. Morita, H., Arisaka, M., Yoshida, N., and Kobayashi, J. (2000) J. Org. Chem., 65, 6241-6245.
170. Morita, H. and Kobayashi, J. (2002) J. Org. Chem., 67, 5378-5381.
171. Katakawa, K., Kitajima, M., Aimi, N., Seki, H., Yamaguchi, K., Furihata, K., Harayama, T., and Takayama, H. (2005) J. Org. Chem., 70, 658-663.
172. Takayama, H., Katakawa, K., Kitajima, M., Yamaguchi, K., and Aimi, N. (2002) Tetrahedron Lett., 43, 8307-8311; (b)
173. Nakayama, A., Kogure, N., Kitajima, M., and Takayama, H. (2009) Org. Lett., 11, 5554-5557
174. Ramharter, J., Weinstabl, H., Mulzer, J. (2010) J. Am. Chem. Soc., 132, 14338-14339.
175. Yang, Y.-R., Shen, L., Wei, K., and Zhao, Q.-S. (2010) J. Org. Chem., 75, 1317-1320.
176. Morita, H., Hirasawa, Y., Shinzato, T., and Kobayashi, J. (2004) Tetrahedron, 60, 7015-7023
177. Ishiuchi, K., Kubota, T., Ishiyama, H., Hayashi, S., Shibata, T., Kobayashi, J. (2011) Tetrahedron Lett., 52, 289-292.
178. Snider, B.B. and Grabowski, J.F. (2007) J. Org. Chem., 72, 1039-1042.
179. Gerard, R.V., MacLean, D.B., Fagianni, R., and Lock, C.J. (1986) Can. J. Chem., 64, 943-949.
180. Liau, B.B. and Shair, M.D. (2010) J. Am. Chem. Soc., 132, 9594-9595.
181. Schumann, D. and Naumann, A. (1983) Liebigs Ann. Chem., 220-225.