Recent synthetic developments in a powerful imino Diels-Alder reaction (Povarov reaction): application to the synthesis of N-polyheterocycles and related alkaloids

Tetrahedron

Volumn 65, Issue 14, 2009, Pages 2721-2750

  Kouznetsov, Vladimir V ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

Author keywords

Alkaloids; Cycloaddition; Intra and intermolecular imino Diels Alder reaction; Polyheterocycles; Povarov reaction; Quinoline derivatives

Indexed keywords

ACRIDINE DERIVATIVE; ALKALOID DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AMIDE; AMINE; AROMATHECIN; CAMPTOTHECIN; CITRONELLAL; HETEROCYCLIC COMPOUND; IMINE; IRINOTECAN; ISOSCHIZOGALINE; LUOTONIN A; MARTINELLIC ACID; MARTINELLINE; NAPHTHYRIDINE DERIVATIVE; PHENANTHROLINE DERIVATIVE; QUINOLINE DERIVATIVE; TOPOTECAN; UNCLASSIFIED DRUG;

CYCLOADDITION; DIELS ALDER REACTION; PRIORITY JOURNAL; REVIEW;

ALNUS;

EID: 61349084177     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.059     Document Type: Review

References (234)

1. Smith M.B. Organic Synthesis. 2nd ed. (2002), Mc Graw-Hill, New York, NY pp 844-849
2. Diels O., and Alder K. Justus Liebigs Ann. Chem. 460 (1928) 98-122
3. Needleman S.B., and Chang Kuo M.C. Chem. Rev. 62 (1962) 405-431
4. Sauer J., and Sustmann R. Angew. Chem., Int. Ed. Engl. 19 (1989) 779-807
5. Kagan H.B., and Riant O. Chem. Rev. 92 (1992) 1007-1019
6. Kumar A. Chem. Rev. 101 (2001) 1-19
7. Nicolaou K.C., Snyder S.A., Montagnon T., and Vassilikogiannakis G. Angew. Chem., Int. Ed. 41 (2002) 1669-1698
8. Corey E.J. Angew. Chem., Int. Ed. 41 (2002) 1650-1667
9. Tringuelli F., and Taticchi A. The Diels-Alder Reaction. Selected Practical Methods (2002), John Wiley, London
10. In: Kobayashi S., and Jørgensen K.A. (Eds). Cycloaddition Reactions in Organic Synthesis (2002), Wiley-VCH, Weinheim
11. Boger D.L., and Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic, San Diego, CA
12. Weinreb S.M. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergmon, Oxford 401-512
13. Buonora P., Olsen J.-C., and Oh T. Tetrahedron 57 (2001) 6099-6138
14. Benforouz M., and Ahmadian M. Tetrahedron 56 (2000) 5259-5288
15. Jørgensen K.A. Angew. Chem., Int. Ed. 39 (2000) 3558-3588
16. Povarov L.S., and Mikhailov B.M. Izv. Akad. Nauk SSR, Ser. Khim. (1963) 953-956
17. Povarov L.S., Grigos V.I., and Mikhailov B.M. Izv. Akad. Nauk SSR, Ser. Khim. (1963) 2039-2041
18. Povarov L.S., Grigos V.I., Karakhanov R.A., and Mikhailov B.M. Izv. Akad. Nauk SSR, Ser. Khim. (1964) 179-186
19. Grigos V.I., Povarov L.S., and Mikhailov B.M. Izv. Akad. Nauk SSR, Ser. Khim. (1965) 2163-2171
20. Povarov L.S., and Mikhailov B.M. Izv. Akad. Nauk SSR, Ser. Khim. (1964) 2221-2222
21. Povarov L.S. Russ. Chem. Rev. 36 (1967) 656-670
22. Taber D.F. Intramolecular Diels-Alder and Alder Ene Reactions (1984), Springer, Berlin
23. Roush W.R. In: Trost B.M., Fleming L.A., and Paquette L.A. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford 513
24. Bear B.R., Sparks S.M., and Shea K.J. Angew. Chem., Int. Ed. 40 (2001) 820-849
25. Katritzky A.R., Rachwal S., and Rachwal B. Tetrahedron 52 (1996) 15031-15070
26. Kouznetsov V., Palma A., Ewert C., and Varlamov A. J. Heterocycl. Chem. 35 (1998) 761-785
27. Kouznetsov V.V., Vargas Méndez L.Y., and Meléndez Gómez C.M. Curr. Org. Chem. 9 (2005) 141-161
28. In: Zhu J., and Bilnaymé H. (Eds). Multicomponent Reactions (2005), Wiley-VCH, Weinheim
29. Orru R.V.A., and de Greef M. Synthesis (2003) 1471-1499
30. Arya P., Joseph R., Gan Z., and Pakic B. Chem. Biol. 12 (2005) 163-180
31. Hermitage S., Jay D.A., and Whiting A. Tetrahedron Lett. (2002) 9633-9636
32. Hermitage S., Howard J.A.K., Jay D.A., Pritchard R.G., Probert M.R., and Whiting A. Org. Biomol. Chem. 2 (2004) 2451-2460
33. Beifuss U., Ledderhose S., and Ondrus V. Arkivoc v (2005) 147-173
34. Alves M.J., Azoia N.G., and Fortes A.G. Tetrahedron 63 (2007) 727-734
35. Mayr H., Ofial A.R., Sauer J., and Schmied B. Eur. J. Org. Chem. (2000) 2013-2020
36. Joh T., and Hagihara H. Tetrahedron Lett. (1967) 4199-4200
37. Kametani T., and Kasai H. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry Vol. 3 (1989), Elsevier, New York, NY 385-389 and references therein
38. Narasaka K., and Shibata T. Heterocycles 35 (1993) 1039-1053
39. Kobayashi S., Ishitani H., and Nagayama S. Synthesis (1995) 1195-1202
40. Kobayashi S., Komlyama S., and Ishitani H. Biotechnol. Bioeng. 61 (1998) 23-31
41. Crousse B., Bégué J.-P., and Bonnet-Delpon D. Tetrahedron Lett. 39 (1998) 5765-5768
42. Crousse B., Bégué J.-P., and Bonnet-Delpon D. J. Org. Chem. 65 (2000) 5009-5013
43. Legros J., Crousse B., Ourévitch M., and Bonnet-Delpon D. Synlett (2006) 1899-1902
44. Collin J., Jaber N., and Lannou M.I. Tetrahedron Lett. 42 (2001) 7405-7407
45. Spanedda M.V., Hoang V.D., Crousse B., Bégué J.-P., and Bonnet-Delpon D.J. Tetrahedron Lett. 44 (2003) 217-219
46. Cho C.S., Kim B.T., Choi H.J., Kim T.J., and Shim S.C. Tetrahedron 59 (2003) 7997-8002
47. Demaude T., Knerr L., and Pasau P. J. Comb. Chem. 6 (2004) 768-775
48. Makioka Y., Shindo T., Taniguchi Y., Takaki K., and Fujiwara Y. Synthesis (1995) 801-804
49. Laurent-Robert H., Garrigues R., and Dubac J. Synlett (2000) 1160-1162
50. Reddy B.V.S., Srinivas R., Yadav J.S., and Ramalingam T. Synth. Commun. 31 (2001) 1075-1080
51. Akiyama T., Nakashima S., Yokota K., and Fuchibe K. Chem. Lett. 33 (2004) 922-923
52. Duvelleroy D., Perrio C., Parisel O., and Lasne M.-C. Org. Biomol. Chem. 3 (2005) 3794-3804
53. Di Salvo A., Spanedda M.V., Ourévitch M., Crousse B., and Bonnet-Delpon D. Synthesis (2003) 2231-2235
54. Sridharan V., Avendaño C., and Menéndez J.C. Tetrahedron 63 (2007) 673-681
55. Park K.H., Joo H.S., Ahn K.I., and Jun K. Tetrahedron Lett. 36 (1995) 5943-5946
56. Ishitani H., and Kobayashi S. Tetrahedron Lett. 37 (1996) 7357-7360
57. Akiyama T., Morita H., and Fuchibe K. J. Am. Chem. Soc. 128 (2006) 13070-13071
58. Sundararajan G., Prabagaran N., and Varghese B. Org. Lett. 3 (2001) 1973-1976
59. Shono T., Matsumura Y., Inoue K., Ohmizu H., and Kashimura S. J. Am. Chem. Soc. 104 (1982) 5753-5757
60. Ha H.-.J., Choi C.-J., Ahn Y.-G., Yun H., Dong Y., and Lee W.K. J. Org. Chem. 65 (2000) 8334-8336
61. Beifuss U., and Ledderhouse S. J. Chem. Soc., Chem. Commun. (1995) 2137-2138
62. Beifuss U., Kunz O., Ledderhouse S., Taraschewski M., and Tonko C. Synlett (1996) 34-36
63. Katrizky A.R., and Belyakov S.A. Aldrichimica Acta 31 (1998) 35-45
64. Katrizky A.R., Rachwal B., and Rachwal S. J. Org. Chem. 58 (1993) 812-813
65. Katrizky A.R., Rachwal B., and Rachwal S. J. Org. Chem. 60 (1995) 2588-2596
66. Chen R., and Quian C. Synth. Commun. 32 (2002) 2543-2548
67. Katrizky A.R., Rachwal B., and Rachwal S. J. Org. Chem. 60 (1995) 7631-7640
68. Talukdar S., Chen C.-T., and Fang J.-M. J. Org. Chem. 65 (2000) 3148-3153
69. Annunziata A., Cinquini M., Molteni V., and Schupp O. Tetrahedron 53 (1997) 9715-9726
70. Annunziata A., Benaglia M., Cinquini M., and Cozzi F. Eur. J. Org. Chem. (2002) 1184-1190
71. Inada T., Nakayuki T., and Shimizu I. Heterocycles 66 (2005) 611-619
72. Tanaka S., Yasuda M., and Baba A. J. Org. Chem. 71 (2006) 860-863
73. Lin X.-F., Cui S.-L., and Wang Y.-G. Tetrahedron Lett. 46 (2006) 3127-3130
74. Nakajima T., Inada T., Igarashi T., Sekioka T., and Shimizu I. Bull. Chem. Soc. Jpn. 79 (2006) 1941-1949
75. Stevenson G., Leeson P.D., Rowley M., Sanderson I., and Stanafield I. Bioorg. Med. Chem. Lett. 2 (1992) 371-374
76. Leeson P.D., Carling R.W., Moore K.W., Moseley A.M., Smith J.D., Stevenson G., Chan T., Baker R., Foster A.C., Grimwood S., Kemp J.A., Marshall G.R., and Hoogsteen K. J. Med. Chem. 35 (1992) 1954-1968
77. Hadden M., Nieuwenhuyezen M., Potts D., Stevenson P.J., and Thompson N. Tetrahedron 57 (2001) 5615-5624
78. Stevenson P.J., and Graham I. Arkivoc vii (2003) 139-144
79. Kiselyov A.S., Smith II L., Virgilio A., and Armstrong R.W. Tetrahedron 54 (1998) 7987-7996
80. Katrizky A.R., Rachwal B., and Rachwal S. J. Org. Chem. 60 (1995) 3993-4001
81. Guinó M., Phua P.H., Caille J.-C., and Hii K.K. J. Org. Chem. 72 (2007) 6290-6293
82. Damon D.B., Dugger R.W., Magnus-Aryitey G., Ruggeri R.B., Wester R.T., Tu M., and Abramov Y. Org. Process Res. Dev. 10 (2006) 464-471
83. Kouznestov V.V., Astudillo Saavedra L., Vargas Méndez L.Y., and Cazar Ramírez M.E. J. Chil. Chem. Soc. 49 (2004) 107-203
84. Kouznestov V.V., Romero Bohórquez A.R., Astudillo Saavedra L., and Fierro Medina R. Mol. Divers. 10 (2006) 29-37
85. Kouznetsov V.V., and Mora Cruz U. Lett. Org. Chem. 3 (2006) 699-702
86. Kouznetsov V.V., Mora Cruz U., Zubkov F.I., and Nikitina E.V. Synthesis (2007) 375-384
87. Zhang W., Guo Y., Liu Z., Jin X., Yang L., and Liu Z.-L. Tetrahedron 61 (2005) 1325-1333
88. Zhou Y., Jia X., Li R., Liu Z., Liu Z., and Wu L. Tetrahedron Lett. 46 (2005) 8937-8939
89. Han B., Jia X.-D., Jin X.-L., Zhou Y.-L., Yang L., Liu Z.-L., and Yu W. Tetrahedron Lett. 47 (2006) 3545-3547
90. Savitha G., and Perumal P.T. Tetrahedron Lett. 47 (2006) 3589-3593
91. Nomura Y., Kimura M., Takeuchi Y., and Tomoda S. Chem. Lett. (1978) 268-270
92. Kametani T., Takeda H., Suzuki Y., and Honda T. Heterocycles 22 (1984) 275-276
93. Fadel F., Titouani S.L., Soufiaoui M., Ajamay H., and Mazzah A. Tetrahedron Lett. 45 (2004) 5905-5908
94. Kouznetsov V.V., Bohórquez Romero A.R., and Stashenko E.E. Tetrahedron Lett. 48 (2007) 8855-8860
95. Kouznetsov V.V., Merchan Arenas D.R., and Bohórquez Romero A.R. Tetrahedron Lett. 49 (2008) 3097-3100
96. Zhang W., Jia X., Yang L., and Liu Z.-L. Tetrahedron Lett. 43 (2002) 9433-9436
97. Jia X., Lin H., Huo C., Zhang W., Lü J., Yang L., and Liu Z.-L. Synlett (2003) 1707-1709
98. Mellor J.M., and Merriman G.D. Tetrahedron 51 (1995) 6115-6132
99. Katrizky A.R., and Gordeev M.F. J. Org. Chem. 58 (1993) 4049-4053
100. Katrizky A.R., Nichols D.A., Qi M., and Yang B. J. Heterocycl. Chem. 34 (1997) 1259-1262
101. Grieco P.A., and Bahsas A. Tetrahedron Lett. 29 (1988) 5855-5858
102. Akiyama T., Suzuki M., and Kagoshima H. Heterocycles 52 (2000) 529-532
103. Hirashita T., Kawai D., and Araki S. Tetrahedron Lett. 48 (2007) 5421-5424
104. Gao K., Li Y., Sun H., Fan R., and Wu J. Synth. Commun. 37 (2007) 4425-4437
105. Baudelle R., Melnyk P., Déprez B., and Tartar A. Tetrahedron 54 (1998) 4125-4140
106. Bortolotti B., Leardini R., Nanni D., and Zanardi G. Tetrahedron 49 (1993) 10157-10174
107. Sueda Huma H.Z., Halder R., Kalra S.S., Das J., and Iqbal J. Tetrahedron Lett. 43 (2002) 6485-6488
108. Yadav J.S., Reddy B.V.S., Rao R.S., Naveenkumar V., and Nagaiah K. Synthesis (2003) 1610-1614
109. Kikuchi S., Iwai M., and Fukuzawa S.-i. Synlett (2007) 2639-2642
110. Sridharan V., Perumal P.T., Avendaño C., and Menéndez J.C. Org. Biomol. Chem. 5 (2007) 1351-1353
111. Tietze L.F. Chem. Rev. 96 (1996) 115-136
112. Laschat S., and Lauterweine J. J. Org. Chem. 58 (1993) 2856-2861
113. Laschat S., Noe R., and Riedel M. Orgametallics 12 (1993) 3738-3742
114. See, excellent review on the transformation of the citronellal:. Lenardão E.J., Botteselle G.V., de Azambuja F., Perin G., and Jacob R.G. Tetrahedron 63 (2007) 6671-6712
115. Kiselyov A.S., Smith II L., and Armstrong R.W. Tetrahedron 54 (1998) 5089-5096
116. Sabitha G., Venkata Reddy E., and Yadav J.S. Synthesis (2002) 409-412
117. Mayekar N.V., Kayak S.K., and Chattopadhyay S. Synth. Commun. 34 (2004) 3111-3119
118. Schulte J.L., Laschat S., Kotila S., Hecht J., Frolich R., and Wibbeling B. Heterocycles 43 (1996) 2713-2724
119. Yadav J.V., Reddy B.V.S., Chetia L., Srinivasulu G., and Kunwar A.C. Tetrahedron Lett. 46 (2005) 1039-1044
120. Jacob R.G., Perin G., Botteselle G.V., and Lenardão E.J. Tetrahedron Lett. 44 (2003) 6809-6812
121. Lenardão E.J., Mendes S.R., Ferreira P.C., Perin G., Silveira C.C., and Jacob R.G. Tetrahedron Lett. 47 (2006) 7439-7442
122. Beifuss U., Herde A., and Ledderhose S. Chem. Commun. (1996) 1213-1214
123. Jones W., and Kiselyov A.S. Tetrahedron Lett. 41 (2000) 2309-2312
124. Nagarajan R., Magesh C.J., and Perumal P.T. Synthesis (2004) 69-74
125. Elamparuthi E., Anniyappan M., Muralidharan D., and Perumal P.T. Arkivoc xi (2005) 6-16
126. Sabitha G., Reddy E.V., and Yadav J.S. Synthesis (2001) 1979-1984
127. Yadav J.S., Reddy B.V.S., Rao R.S., and Srinivas R. Synlett (2002) 993-995
128. Anniyappan M., Muralidharan D., and Perumal P.T. Tetrahedron Lett. 44 (2003) 3653-3657
129. Znang D., and Kiselyov A.S. Synlett (2001) 1173-1175
130. Spaller M.R., Thielemann W.T., Brennan P.E., and Bartlett P.A. J. Comb. Chem. 4 (2002) 516-522
131. Sabitha G., Reddy V.E., Maruthi Ch., and Yadav J.S. Tetrahedron Lett. 43 (2002) 1573-1575
132. Skotnicki J.S., Steinbaugh B.A., Fitzgerald Jr. J.J., Kearney R.M., Mosser J.H., Adams L.M., Caccere R.G., Chang J.Y., and Gilman S.C. Med. Chem. Res. 1 (1991) 245-251
133. Bertenshaw S.R., Talley J.J., Rogier D.J., Graneto M.J., Koboldt C.M., and Zhang Y. Bioorg. Med. Chem. Lett. 6 (1996) 2827-2830
134. Sabitha G., Reddy S., Maruthi E., Reddy V., and Yadav J.S. Synth. Commun. 33 (2003) 3063-3070
135. Manian R.D.R.S., Jayashankaran J., Ramesh R., and Raghunathan R. Tetrahedron Lett. 47 (2006) 7571-7574
136. Sabitha G., Reddy V.E., Yadav J.S., Krishna K.V.S.R., and Sankar A.R. Tetrahedron Lett. 43 (2002) 4029-4032
137. Sharma G.V.M., Srinivas Reddy I., Goverdhan Reddy V., and Rama Rao A.V. Tetrahedron: Asymmetry 10 (1999) 229-235
138. Kiselyov A.S. Synlett (2006) 391-394
139. Muhuni J., and Spaller M.R. J. Org. Chem. 71 (2006) 5515-5526
140. Linkert F., and Laschat S. Synlett (1994) 125-126
141. Linkert F., Laschat S., Kotila S., and Fox T. Tetrahedron 52 (1996) 955-970
142. Temme O., Dickner T., Laschat S., Fröhlich R., Kotila S., and Bergander K. Eur. J. Org. Chem. (1998) 651-659
143. Temme O., and Laschat S. J. Chem. Soc., Perkin Trans. 1 (1995) 125-131
144. Laschat S., and Grehl M. Chem. Ber. (1994) 125-126
145. Gaddam V., and Nagarajan R. Tetrahedron Lett. 48 (2007) 7335-7338
146. Ramesh E., and Raghunathan R. Tetrahedron Lett. 49 (2008) 2583-2586
147. Wall M.E., Wani M.C., Cook C.E., Palmer K.H., MacPhail A.T., and Sim G.A. J. Am. Chem. Soc. 88 (1966) 3888-3890
148. Thomas C.J., Rahier N.J., and Hecht S.M. Bioorg. Med. Chem. 12 (2004) 1585-1604
149. Lin L.Z., and Cordell G.A. Phytochemistry 28 (1989) 1295-1297
150. First total synthesis, see:. Ma Z., and Lee D.Y.W. Tetrahedron Lett. 45 (2004) 6721-6723
151. Xiao X., Antony S., Pommier Y., and Cushman M. J. Med. Chem. 49 (2006) 1408-1412
152. Ma Z.-Z., Hano Y., Nomura T., and Chen Y.-J. Heterocycles 46 (1997) 541-546
153. Twin H., and Batey R.A. Org. Lett. 6 (2004) 4913-4916
154. Eckert H. Angew. Chem., Int. Ed. Engl. 20 (1981) 208-210
155. Zhou H.-B., Liu G.-S., and Yao Z.-J. J. Org. Chem. 72 (2007) 6270-6272
156. Zhou H.-B., Liu G.-S., and Yao Z.-J. Org. Lett. 9 (2007) 2003-2006
157. See, another approach to luotonin A, based on intramolecular imino DA reaction:. Toyota M., Komori C., and Ihara M. Heterocycles 56 (2002) 101-103
158. Gaddam V., and Nagarajan R. Org. Lett. 10 (2008) 1975-1978
159. Renner U., and Kemweisz P. Experientia 19 (1963) 244-246
160. Magomedov N.A. Org. Lett. 5 (2003) 2509-2512
161. Zhou J., and Magomedov N.A. J. Org. Chem. 72 (2007) 3808-3815
162. Wölfling J., Frank E., Schneider G., and Tietze L.F. Eur. J. Org. Chem. (1999) 3013-3020
163. Shvekhgeimer M.-G.A. Russ. Chem. Rev. 66 (1997) 151-178
164. Kobayashi S. Pure Appl. Chem. (1998) 1019-1026
165. Yamamoto H. Lewis Acids in Organic Synthesis (2000), Wiley-VHC, New York, NY
166. Kobayashi S., Sugiura M., Kitagawa H., and Lam W.W.-L. Chem. Rev. 102 (2002) 2227-2302
167. Maiti G., and Kundu P. Tetrahedron Lett. 47 (2006) 5733-5736
168. Ma Y., Qian C., Xie M., and Sun J. J. Org. Chem. 64 (1999) 6462-6467
169. Babu G., and Perumal P.T. Tetrahedron Lett. 39 (1998) 3225-3228
170. Yadav J.S., Reddy B.V.S., Madhuri C.R., and Sabatha G. Synthesis (2001) 1065-1068
171. Mahajan D., Ganai B.A., Sharma R.L., and Kapoor K.K. Tetrahedron Lett. 47 (2006) 7919-7921
172. Mahesh M., Venkateswar Reddy C., Srinivasa Reddy K., Raju P.V.K., and Narayana Reddy V.V. Synth. Commun. 34 (2004) 4089-4104
173. Das B., Ravinder Reddy M., Saidi Reddy V., and Ramu R. Chem. Lett. 33 (2004) 1526-1527
174. Semwal A., and Nayak S.K. Synth. Commun. 36 (2006) 227-236
175. Xia M., and Lu Y.-d. Synlett (2005) 2357-2361
176. More S.V., Sasty M.N.V., and Yao C.-F. Synlett (2006) 1399-1403
177. Srinivas K.V.N.S., and Das B. Synlett (2004) 1715-1718
178. Nagaiah K., Sreenu D., Rao R.S., Vashita G., and Yadav J.S. Tetrahedron Lett. 46 (2006) 4409-4413
179. Ravindranath N., Ramesh C., Ravinder Reddy M., and Das B. Chem. Lett. 32 (2003) 222-223
180. Masaki Y., Yamada T., Kawai H., Itoh A., Arai Y., and Furukawa H. Synlett (2006) 288-290
181. Yadav J.S., Reddy B.V.S., Sumitha V., and Reddy K.S. Adv. Synth. Catal. 345 (2003) 1203-1206
182. Shao L.-X., and Shi M. Adv. Synth. Catal. 345 (2003) 963-966
183. Zhou Z., Xu F., Han X., Zhou J., and Shen Q. Eur. J. Org. Chem. 31 (2007) 5265-5269
184. Xing X., Wu J., and Dai W.-M. Tetrahedron 62 (2006) 11200-11206
185. da Silva-Filho L.C., Júnior V.L., Constantino M.G., and da Silva G.V.J. Synthesis (2008) 2527-2536
186. Hoemann M.Z., Xie R.L., Rossi R.F., Meyer S., Sidhu A., Cuny G.D., and Hauske J.R. Bioorg. Med. Chem. Lett. 12 (2002) 129-132
187. Zulykama Y., Nagarajan R., and Perumal P.T. Synth. Commun. (2004) 1309-1315
188. Kumar R.S., Nagarajan R., Vijav K., and Perumal P.T. Lett. Org. Chem. 2 (2005) 458-460
189. Kumar R.S., Nagarajan R., and Perumal P.T. Synthesis (2004) 949-959
190. Gaddam V., Sreenivas D.K., and Nagarajan R. Tetrahedron Lett. 47 (2006) 9291-9295
191. Wang J., Xu F.-X., Lin X.-F., and Wang Y.-G. Tetrahedron Lett. 49 (2008) 5208-5210
192. Loh T.-P., Pei J., and Lin M. Chem. Commun. (1996) 2315-2316
193. Zhang J., and Li C.-J. J. Org. Chem. 67 (2002) 3969-3971
194. Yadav J.S., Reddy B.V.S., Rao R.S., Kiran S.K., and Kunwar A.C. Tetrahedron 58 (2002) 7891-7896
195. Batey R., Powell D.A., Acton A., and Lough A.J. Tetrahedron Lett. 42 (2001) 7935-7939
196. Chen L., and Li C.-J. Green Chem. 5 (2003) 627-629
197. Yadav J.S., Reddy B.V.S., Sadasiv K., and Reddy P.S.R. Tetrahedron Lett. 43 (2002) 3853-3856
198. Yadav J.S., Reddy B.V.S., Gayathri K.U., and Prasad A.R. Synthesis (2002) 2537-2541
199. Chen L., Li Z., and Li C.-J. Synlett (2003) 732-734
200. Kamal A., Prasad B.R., Ramana A.V., Babu A.H., and Reddy K.S. Tetrahedron Lett. 45 (2004) 3507-3509
201. Mandagopal S., Gatha B., and Perumal P.T. Synth. Commun. 34 (2004) 1157-1161
202. Babu G., and Perumal P.T. Tetrahedron 55 (1999) 4793-4802
203. Kobayashi S., and Nagayama S. J. Am. Chem. Soc. 118 (1996) 8977-8978
204. Posson H., Hurvois J.-P., and Moinet C. Synlett (2000) 209-212
205. Sartori G., Bigi F., Maggi R., Mazzacani A., and Oppici G. Eur. J. Org. Chem. (2001) 2513-2518
206. Ramesh E., Elamparuthi E., and Raghunathan R. Synth. Commun. 36 (2006) 1431-1436
207. Shinji, O.; Tetsuji, A.; Keisuke, I.; Masato, W.; Teruhiro, U.; Juji, Y. Japan Patent 09052879, 1997;
208. Chem. Abstr. 126 (1997) 238311x
209. Anzini M., Cappelli A., and Vomero S. J. Heterocycl. Chem. 28 (1991) 1809-1812
210. Rampa A., Bisi A., Belluti F., Gobbi S., Valenti P., Andrisano V., Cavrini V., Cavalli A., and Recanatini M. Bioorg. Med. Chem. 8 (2000) 497-506
211. Byl J.A.W., Fortune J.M., Burden D.A., Nitiss J.L., Utsugi T., Yamada Y., and Osheroff N. Biochemistry 38 (1999) 15573-15579
212. Fortune J.M., Velea L., Graves D.E., Utsugi T., Yamada Y., and Osheroff N. Biochemistry 38 (1999) 15580-15586
213. Kluza J., Lansiaux A., Wattez N., Mahieu C., Osheroff N., and Bailly C. Cancer Res. 60 (2000) 4077-4084
214. Mizutani H., Tada-Oikawa S., Hiraku Y., Oikawa S., Kojima M., and Kawanishi S. J. Biol. Chem. 277 (2002) 30684-30689
215. Ewesuedo R.B., Iyer L., Das S., Koenig A., Mani S., Vogelzang N.J., Schilsky R.L., Brenckman W., and Ratain M.J. J. Clin. Oncol. 19 (2001) 2084-2090
216. Ishida K., and Asao T. Biochim. Biophys. Acta 1587 (2002) 155-163
217. Kouznetsov V.V., Ochoa Puentes C., Bohórquez Romero A.R., Zacchino S.A., Sortino M., Gupta M., Vázquez Y., Bahsas A., and Amaro-Luis J. Lett. Org. Chem. 3 (2006) 300-304
218. Witherup K.M., Ransom R.W., Graham A.C., Bernard A.M., Salvatore M.J., Lumma W.C., Anderson P.S., Pitzenberger S.M., and Varga S.L. J. Am. Chem. Soc. 117 (1995) 6682-6685
219. Judd W.R., and Aubé J. Chemtracts: Org. Chem. 16 (2003) 105-116
220. Nyerges M. Heterocycles 63 (2004) 1685-1712
221. First asymmetric total synthesis of (-)-martinelline, see. Ikeda S., Shibuya M., and Iwabuchi Y. Chem. Commun. (2007) 504-506
222. Batey R.A., Simoncic P.D., Lin D., Smyj R.P., and Lough A.J. Chem. Commun. (1999) 651-652
223. Hadden M., and Stevenson P.J. Tetrahedron Lett. 40 (1999) 1215-1218
224. Hadden M., Nieuwenhuyzen M., Osborne D., Stevenson P.J., and Thompson N. Tetrahedron Lett. 42 (2001) 6417-6419
225. Xia C., Heng L., and Ma D. Tetrahedron Lett. 43 (2002) 9405-9409
226. Powell D.A., and Batey R.A. Org. Lett. 4 (2002) 2913-2916
227. Batey R.A., and Powell D.A. Chem. Commun. (2001) 2362-2363
228. Yadav J.S., Reddy B.V.S., Sunitha V., Reddy K.S., and Ramakrishna K.V.S. Tetrahedron Lett. 45 (2004) 7947-7950
229. Dave P.R., Duddu R., Surapaneni R., and Gilardi R. Tetrahedron Lett. 40 (1999) 443-446
230. Stevenson P.J., Nieuwenhuyzen M., and Osborne D. Chem. Commun. (2002) 444-445
231. Stevenson P.J., Nieuwenhuyzen M., and Osborne D. Arkivoc xi (2007) 129-144
232. Osborne D., and Stevenson P.J. Tetrahedron Lett. 43 (2002) 5469-5470
233. Wang H.S., and Ganesan A. Tetrahedron Lett. 39 (1998) 9097-9098
234. Yadav J.S., and Reddy B.V.S. Tetrahedron Lett. 43 (2002) 1905-1908