Application of hydrolytic kinetic resolution (HKR) in the synthesis of bioactive compounds

Tetrahedron

Volumn 63, Issue 13, 2007, Pages 2745-2785

  Kumar, Pradeep ^a   Naidu, Vasudeva ^a   Gupta, Priti ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Biological activity; Bis epoxides; Hydrolytic kinetic resolution; meso Epoxides; Natural products; Synthesis; Terminal epoxides

Indexed keywords

ACETOGENIN; AMPHIDINOLIDE A; AROMATIC COMPOUND; ARUNDIC ACID; ATENOLOL; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; BETAXOLOL; BORON DERIVATIVE; BREVETOXIN; CARNITINE DERIVATIVE; CMI 977; DIHYDROBENZOFURAN DERIVATIVE; EPOTHILONE A; EPOXIDE; ETHER DERIVATIVE; FOSTRIECIN; GLYCIDOL; IMINE; INDOLIZIDINE DERIVATIVE; LACTONE DERIVATIVE; LAULIMALIDE; LDP 977; MACROLIDE; NAFTOPIDIL; NATURAL PRODUCT; OLIGOMER; PHENYLEPHRINE; PHEROMONE; PHOSPHATIDIC ACID; PHOSPHONIC ACID DERIVATIVE; POLYENE; SCH 642305; THIOCTIC ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ASTROCYTE; BIOLOGICAL ACTIVITY; CARDIOVASCULAR DISEASE; CATALYST; CELL ACTIVATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG ACTIVITY; DRUG SYNTHESIS; EPOXIDATION; GLAUCOMA; HALOGENATION; HEART ARRHYTHMIA; HUMAN; HYDROLYTIC KINETIC RESOLUTION; HYPERTENSION; NONHUMAN; OLIGOMERIZATION; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 33847220338     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.015     Document Type: Review

References (253)

1. Johnson R.A., and Sharpless K.B. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis (1993), VCH, New York, NY Chapter 4.1
2. In: Jacobsen E.N. (Ed) (1993), VCH, New York, NY Chapter 4.2
3. Tokunaga M., Larrow J.F., Kakiuchi F., and Jacobsen E.N. Science 277 (1997) 936-938
4. Schaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., Furrow M.E., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 1307-1315
5. For information, see: http://www.Rhodiachirex.com
6. Aouni L., Hemberger K.E., Jasmin S., Kabir H., Larrow J.R., Le-Fur I., Morel P., and Schlama T. Industrialization Studies of the Jacobsen Hydrolytic Kinetic Resolution of Epichlorohydrin. In: Blaser H.U., and Schmidt E. (Eds). Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions (2004), Wiley, Germany 165-199
7. Larrow J.F., Hemberger K.E., Jasmin S., Kabir H., and Morel P. Tetrahedron: Asymmetry 14 (2003) 3589-3592
8. Larrow, J. F.; Hemberger, K. E.; Kabir, H.; Morel, P. Active Catalysts for Stereoselective Ring-opening Reactions. U.S. Patent 6,781,006, 2004;
9. Martinez L.E., Leighton J.L., Carsten D.H., and Jacobsen E.N. J. Am. Chem. Soc. 117 (1995) 5897-5898
10. Lebel H., and Jacobsen E.N. Tetrahedron Lett. 40 (1999) 7303-7306
11. For various types of oligomeric catalysts, see:
12. Reddy J.M., and Jacobsen E.N. J. Am. Chem. Soc. 123 (2001) 2687-2688
13. Reddy J.M., and Jacobsen E.N. Angew Chem., Int. Ed. 41 (2002) 1374-1377
14. White D.E., and Jacobsen E.N. Tetrahedron: Asymmetry 14 (2003) 3633-3638
15. Zheng X., Jones C.W., and Weck M. Chem.-Eur. J. 12 (2006) 576-583
16. Li W., Thakur S.S., Chen S.-W., Shin C.-K., Kawthekar R.B., and Kim G.-J. Tetrahedron Lett. 47 (2006) 3453-3457
17. Thakur S.S., Li W., Shin C.-K., and Kim G.-J. Catal. Lett. 104 (2005) 151-156
18. Thakur S.S., Li W., Shin C.-K., and Kim G.-J. Chirality 18 (2006) 37-43
19. Thakur S.S., Li W., Kim S.-J., and Kim G.-J. Tetrahedron Lett. 46 (2005) 2263-2266
20. Shin C.-K., Kim S.-J., and Kim G.-J. Tetrahedron Lett. 45 (2004) 7429-7433
21. Song Y., Chen H., Hu X., Bai C., and Zheng Z. Tetrahedron Lett. 44 (2003) 7081-7085
22. Kwon M., and Kim G.-J. Catal. Today 87 (2003) 145-151
23. Song Y., Yao X., Chen H., Bai C., Hu X., and Zheng Z. Tetrahedron Lett. 43 (2002) 6625-6627
24. Holbach M., and Weck M. J. Org. Chem. 71 (2006) 1825-1836
25. Movassaghi M., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 2456-2457
26. Breimbauer R., and Jacobsen E.N. Angew Chem., Int. Ed. 39 (2000) 3604-3607
27. Annis D.A., and Jacobsen E.N. J. Am. Chem. Soc. 121 (1999) 4147-4154
28. Shi G., Kozlowski J.F., Schwedler J.T., Wood K.V., MacDougal J.M., and McLaughlin J.L. J. Org. Chem. 61 (1996) 7988-7989
29. Schaus S.E., Branalt J., and Jacobsen E.J. J. Org. Chem. 63 (1998) 4876-4877
30. Schaus S.E., Branalt J., and Jacobsen E.J. J. Org. Chem. 63 (1998) 403-405
31. Woollard P.M. Biochem. Biophys. Res. Commun. 136 (1986) 169-176
32. Hamberg M., and Samuelsson B. Proc. Natl. Acad. Sci. U.S.A. 71 (1974) 3400-3404
33. Dailey L.A., and Imming P. Curr. Med. Chem. 6 (1999) 389-398
34. Ford-Hutchinson A.W. Crit. Rev. Immunol. 10 (1990) 1-12
35. Gosselin, J.; Borgeat, P. (Virocell Inc.). U.S. Patent 5,789,441, 1998.
36. Rodriguez A., Nomen M., Spur B.W., Godfroid J.J., and Lee T.H. Tetrahedron 57 (2001) 25-37
37. Cai X., Cheah S., Chen S.M., Eckman J., Ellis J., Fisher R., Fura A., Grewal G., Hussion S., Ip S., Killian D.B., Garahan L.-L., Lounsbury H., Qian C.G., Scannell R.T., Yaeger D., Wypij D.M., Yeh C.G., Young M.A., and Yu S.X. Abstr. Pap.-Am. Chem. Soc. 214 (1997) 214-MEDI
38. Press release from Millenium Pharmaceuticals, Cambridge, USA, 10th October, 2000.
39. Gurjar M.K., Murugaiah A.M.S., Radhakrishna P., Ramana C.V., and Chorghade M.S. Tetrahedron: Asymmetry 14 (2003) 1363-1370
40. Serhan C.N. Curr. Opin. Clin. Nutr. Metab. Care 8 (2005) 115-121
41. Rodriguez A.R., and Spur B.W. Tetrahedron Lett. 46 (2005) 3623-3627
42. Heitz M.-P., Wagner A., Mioskowski C., Noel J.-P., and Beaucourt J.-P. J. Org. Chem. 54 (1989) 500-503
43. Nicolaou K.C., and Webber S.E. J. Am. Chem. Soc. 106 (1984) 5734-5736
44. Bundgard H., Buur A., chang S.C., and Lee V.H.L. Int. J. Pharm. 46 (1988) 77-88
45. Bundgard H., Buur A., Chang S.C., and Lee V.H.L. Int. J. Pharm. 33 (1986) 15-26
46. Sorensen S.J., and Abel S.R. Ann. Pharmacother. 30 (1996) 43-54
47. Bose D.S., and Narsaiah A.V. Bioorg. Med. Chem. 13 (2005) 627-630
48. Drugs Future 12 (1987) 31
49. Kothakonda K.K., and Bose D.S. Chem. Lett. 33 (2004) 1212-1213
50. Bose D.S., Reddy A.V.N., and Chavhan S.W. Synthesis 14 (2005) 2345-2348
51. Reza M., and Dion R.B. J. Pharm. Sci. 4 (2001) 185-200
52. Bodor N., El-Koussi A.A., Kano M., and Khalifa M.M. J. Med. Chem. 31 (1988) 1651-1656
53. Robinson C.P. Drugs Today 22 (1986) 213-219
54. Morrselli, P. L.; De Santis, L., Jr.; Adamski, R. U.S. Patent 4,342,783, 1982;
55. Morrselli P.L., De Santis Jr. L., and Adamski R. Chem. Abstr. 97 (1982) 168936
56. Joshi R.A., Garud D.R., Muthukrishnan M., Joshi R.R., and Gurjar M.K. Tetrahedron: Asymmetry 16 (2005) 3802-3806
57. Floreancig P.E., Swalley S.E., Trauger J.W., and Dervan P.B. J. Am. Chem. Soc. 122 (2000) 6342-6350
58. Yadav J.S., and Rajaiah G. Synlett (2004) 1743-1746
59. Roth H.J., and Kleemann A. Pharmaceutical Chemistry Vol. 1 (1988), Ellis Horwood, Chichester, UK p 41
60. Gurjar M.K., Krishna L.M., Sarma B.V.N.B.S., and Chorghade M.S. Org. Process Res. Dev. 2 (1998) 422-424
61. Rodriguez A.R., and Spur B.W. Tetrahedron Lett. 44 (2003) 7411-7415
62. Gupta P., Naidu S.V., and Kumar P. Tetrahedron Lett. 45 (2004) 849-851
63. Cameron J.S., Abbanat D., Bernan V.S., Maiese W.M., Greenstein M., Jompa J., and Ireland C.M. J. Nat. Prod. 63 (2000) 142-145
64. Hirota H., Hirota A., Sakai H., Isogai A., and Takahashi T. Bull. Chem. Soc. Jpn. 58 (1985) 2147-2148
65. Hirota A., Sakai H., and Isogai A. Agric. Biol. Chem. 49 (1985) 731-735
66. Fujii Y., Fukuda A., Hamasaki T., Ichimoto I., and Nakajima H. Phytochemistry 40 (1995) 1443-1446
67. Pandey S.K., and Kumar P. Tetrahedron Lett. 46 (2005) 6625-6627
68. Czerwonka R., Reddy K.R., Baum E., and Knölker H.-J. Chem. Commun. (2006) 711-713
69. Wu Y., and Sun Y.-P. Org. Lett. 8 (2006) 2831-2834
70. Nielsen L.B., and Wege D. Org. Biomol. Chem. 4 (2006) 868-876
71. Roulland E., and Ermolenko M.S. Org. Lett. 7 (2005) 2225-2228
72. Knölker H.-J., Baum E., and Reddy K.R. Tetrahedron Lett. 41 (2000) 1171-1174
73. Kopitz J. Glycolipids: Structure and Function. In: Gabius H.-J., and Gabius S. (Eds). Glycosciences, Status and Perspectives (1997), Chapman and Hall, New York, NY 163-189
74. Vankar Y.D., and Schmidt R.R. Chem. Soc. Rev. 29 (2000) 201-216
75. Lafont D., Bouchu M.-N., Girard-Egrot A., and Boullanger P. Carbohydr. Res. 336 (2001) 181-194
76. Paddon-Jones G.C., McErlean C.S.P., Hayes P., Moore C.J., Konig W.A., and Kitching W. J. Org. Chem. 66 (2001) 7487-7495
77. For recent reviews on amphidinolides, see:
78. Kobayashi J., and Tsuda M. Nat. Prod. Rep. 21 (2004) 77-93
79. Chakraborty T.K., and Das S. Curr. Med. Chem.: Anti-Cancer Agents 1 (2001) 131-149
80. Kobayashi J., Ishibashi M., and Mori K. Comprehensive Natural Products Chemistry Vol. 8 (1999), Elsevier, New York, NY 619-649
81. O'Brien K.C., Colby E.A., and Jamison T.F. Tetrahedron 61 (2005) 6243-6248
82. Baylon C., Heck M.P., and Mioskowski C. J. Org. Chem. 64 (1999) 3354-3360
83. Colby E.A., O'Brien K.C., and Jamison T.F. J. Am. Chem. Soc. 126 (2004) 998-999
84. Nascimento I.R., and Lopes L.M.X. Phytochemistry 52 (1999) 345-350
85. Ishii H., and Ishikawa T. Tetrahedron Lett. 23 (1982) 4345-4348
86. Helberg M.R., Namil A., Delgado P., David K.C., Kessler T.L., Graff G., Haggard K.S., and Nixon J.C. J. Med. Chem. 42 (1999) 267-276
87. Pfefferle W., Anke H., Bross M., Steffan B., Vianden R., and Steglich W. J. Antibiot. 43 (1990) 648-654
88. Jarvis B.B., Pena B.N., Comezoglu N.S., and Rao M.M. Phytochemistry 25 (1986) 533-535
89. Achenbach H., Usubillaga A., Utz W., and Rodriguez H.A. Phytochemistry 30 (1991) 3753-3757
90. Bhoga U. Tetrahedron Lett. 46 (2005) 5239-5242
91. Kigoshi H., Niwa H., Yamada K., Stout T.J., and Clardy J. Tetrahedron Lett. 32 (1991) 2427-2428
92. Kobayashi K., Shimogawa H., Sakakura A., Teruya T., Suenaga K., and Kigoshi H. Chem. Lett. 33 (2004) 1262-1263
93. Tateishi, N.; Ohno, H.; Kishimoto, K.; Ohuchida. JP 7-316092, 1995;
94. Matusui T., Mori T., Tateishi N., Kagamiishi Y., Satoh S., Katsube N., Morikawa E., Morimoto T., Ikuta F., and Asano T. J. Cereb. Blood Flow Metab. 22 (2002) 711-722
95. Tateishi N., Mori T., Matsui T., and Asano T. J. Cereb. Blood Flow Metab. 22 (2002) 723-734
96. Hasegawa T., Kawanaka Y., Kasamatsu E., Ohta C., Nakabayashi K., Okamoto M., Hamano M., Takahashi K., Ohuchida S., and Hamada Y. Org. Process Res. Dev. 9 (2005) 774-781
97. Gries R., Khaskin G., Gries G., Bennett R.G., King G.G.S., Morewood P., Slessor K.N., and Morewood W.D. J. Chem. Ecol. 28 (2002) 2283-2297
98. Bernsmann H., Hungerhoff B., Fechner R., Fröhlich R., and Metz P. Tetrahedron Lett. 41 (2000) 1721-1724
99. Kojima N., Maezaki N., Tominaga H., Asai M., Yanai M., and Tanaka T. Chem.-Eur. J. 9 (2003) 4980-4990
100. Cloninger M.J., and Overman L.E. J. Am. Chem. Soc. 121 (1999) 1092-1093
101. Ishiyama H., Ishibashi M., Ogawa A., Yoshida S., and Kobayashi J. J. Org. Chem. 52 (1997) 3831-3836
102. Lebel H., and Jacobsen E.N. J. Org. Chem. 63 (1998) 9624-9625
103. Hou X.-L., Li B.-F., and Dai L.-X. Tetrahedron: Asymmetry 10 (1999) 2319-2326
104. Vaughan Williams M. In: Szekeres L. (Ed). Pharmacology Antiarrhythmic Agents (1981), Pergamon, Oxford
105. Malawska B., Gorczyca M., and Filipek B. Pol. J. Pharmacol. Pharm. 44 (1992) 561-574
106. Filipek B., Sapa J., Malawska B., Kulig K., and Antkiewicz-Michaluk L. Arch. Pharm. Pharm. Med. Chem. 330 (1997) 225-231
107. Filipek, B.; Malawska, B.; Kulig, K.; Sapa, J. Polish Patent Application P-319983, 1997.
108. Kulig K., Holzgrabe U., and Malawska B. Tetrahedron: Asymmetry 12 (2001) 2533-2536
109. Tunac J.B., Graham B.D., and Dobson W.E. J. Antibiot. 36 (1983) 1595-1600
110. Stampala S.S., Bunge R.H., Hurley T.R., Willmer N.E., Brankiewicz A.J., Steinman C.E., Smitka T.A., and French J.C. J. Antibiot. 36 (1983) 1601-1605
111. Hokanson G.C., and French J.C. J. Org. Chem. 50 (1985) 462-466
112. For reviews, see:
113. Jackson R.C., Fry D.W., Boritzki T.J., Roberts B.J., Hook K.E., and Leopold W.R. Adv. Enzyme Regul. 23 (1985) 193-215
114. De Jong R.S., De Vries E.G.E., and Mulder N.H. Anti-Cancer Drugs 8 (1997) 413-418
115. Chavez D.E., and Jacobsen E.N. Angew. Chem., Int. Ed. 40 (2001) 3667-3670
116. Wellman G.R., Lam B., Anderson E.L., and White E. Synthesis (1976) 547-548
117. Roesener J.A., and Scheuer P.J. J. Am. Chem. Soc. 108 (1986) 846-847
118. Celatka C.A., and Panek J.S. Tetrahedron Lett. 43 (2002) 7043-7046
119. Liu P., and Panek J.S. J. Am. Chem. Soc. 122 (2000) 1235-1236
120. Hofle, G.; Bedorf, N.; Gerth, K.; Reichenbach, H. DE 4138042, 1993;
121. Chem. Abstr. 120 (1993) 52841
122. Hofle G., Bedorf N., Steinmetz H., Schomburg D., Gerth G., and Reichenbach H. Angew. Chem., Int. Ed. 35 (1996) 1567-1569
123. Hardt I.H., Steinmetz H., Gerth K., Sasse F., Reichenbach H., and Hofle G. J. Nat. Prod. 64 (2001) 847-856
124. Liu Z.-Y., Chen Z.-C., Yu C.-Z., Wang R.-F., Zhang R.-Z., Huang C.-S., Yan Z., Cao D.-R., Sun J.-B., and Li G. Chem.-Eur. J. 8 (2002) 3747-3756
125. Mori I., Ishihara K., and Heathcock C.H. J. Org. Chem. 64 (1990) 2164-2165
126. Taber D.F., and Houze J.B. J. Org. Chem. 59 (1994) 4004-4006
127. Liu Z.-Y., Yu C.-Z., and Yang J. Synlett (1997) 1383-1384
128. Liu Z.-Y., Yu C.-Z., Liu Z.-Y., Yu C.-Z., and Li G. Tetrahedron Lett. 39 (1998) 5261-5264
129. Gao Y., Hanson R.M., Klunder J.M., Ko S.Y., Masamune H., and Sharpless K.B. J. Am. Chem. Soc. 109 (1987) 5765-5780
130. Hooper F.E., and Johnson T.B. J. Am. Chem. Soc. 56 (1934) 470-471
131. Miyauchi M., Endo R., Hisaoka M., Yasuda H., and Kawamoto I. J. Antibiot. 50 (1997) 429-439
132. Mulzer J., Zuhse R., and Schmiechem R. Angew. Chem., Int. Ed. Engl. 31 (1992) 870-872
133. Pifferi, G.; Pinza, M. U.S. Patent 4,118,396, 1978;
134. Aschwanden, W.; Kyburz, E. U.S. Patent 4,476,308, 1984;
135. Iriuchijima, S.; Kobayashi, H.; Aoki, K.; Oda, T.; Shinoyama, M.; Nosaka, Y. U.S. Patent 4,686,296, 1987;
136. Pinza, M.; Pfeiffer, U. C. U.S. Patent 4,797,496, 1989.
137. Jeong Y.-C., Hwang S.K., and Ahn K.-H. Bull. Korean Chem. Soc. 26 (2005) 826-828
138. Chow S., and Kitching W. Chem. Commun. (2001) 1040-1041
139. Rupprecht J.K., Hui Y.H., and McLaughlin J.L. J. Nat. Prod. 53 (1990) 237-278
140. Fang X.P., Rieser M.J., Gu Z.M., and McLaughlin J.L. Phytochem. Anal. 4 (1993) 27-67
141. Zeng L., Ye Q., Oberlies N.H., Shi G.E., Gu Z.M., He K., and McLaughlin J.L. Nat. Prod. Rep. (1996) 275-306
142. Cave A., Figadre B., Laurens A., and Cortes D. Prog. Chem. Org. Nat. Prod. 70 (1997) 81-88
143. Yu Q., Wu Y., Xia L.-J., Tang M.-H., and Wu Y.-L. Chem. Commun. (1999) 129-130
144. Yao Z.J., and Wu Y.L. Tetrahedron Lett. 35 (1994) 157-160
145. Lochyński S., Fra{ogonek}ckowiak B., Librowski T., Czarnecki R., Grochowski J., Serda P., and Gierula M.P. Tetrahedron: Asymmetry 13 (2002) 873-878
146. Kang B., and Chang S. Tetrahedron 60 (2004) 7353-7359
147. Rychnovsky S.D. Chem. Rev. 95 (1995) 2021-2040
148. Gupta P., Naidu S.V., and Kumar P. Tetrahedron Lett. 46 (2005) 6571-6573
149. Kumar P., Gupta P., and Naidu S.V. Chem.-Eur. J. 12 (2005) 1397-1402
150. Choi M.-Y., Khaskin G., Gries R., Gries G., Roitber B.D., Raworth D.A., Kim D.-H., and Bennett R.G. J. Chem. Ecol. 30 (2004) 659-670
151. Gries R., Gries G., Khaskin G., King S., Olfert O., Kaminski L.-A., Lamb R., and Bennett R. Naturwissenschaften 87 (2000) 450-454
152. Krishna P.R., and Reddy V.V.R. Tetrahedron Lett. 46 (2005) 3905-3907
153. Davies-Coleman M.T., and Rivett D.E.A. Fortschr. Chem. Org. Naturst. 55 (1989) 1-35
154. Ohloff G. Fortschr. Chem. Org. Naturst. 35 (1978) 431-527
155. Aditychaudhury N., and Das A.K. J. Sci. Ind. Res. 38 (1979) 265-277
156. Siegel S.M. Phytochemistry 15 (1976) 566-567
157. Davies-Coleman M.T., and Rivett D.E.A. Phytochemistry 26 (1987) 3047-3050
158. Watt J., and Brandwijik M.G.B. The Medicinal and Poisonous Plants of Southern and Eastern Africa (1962), Livingston, Edinburgh p 516
159. Kumar P., and Naidu S.V. J. Org. Chem. 71 (2006) 3935-3942
160. Burova S.A., and McDonald F.E. J. Am. Chem. Soc. 126 (2004) 2495-2500
161. Hyodo, T.; Tsuchiya, Y.; Sekine, A.; Amano, T. Jpn. Kokai Tokkyo Koho 11246587, Sept 14, 1999.
162. Takahashi S., Souma K., Hashimoto R., Koshino H., and Nakata T. J. Org. Chem. 69 (2004) 4509-4515
163. Kim Y.-J., and Tae J. Synlett (2006) 61-64
164. Radl S., Stach J., and Hajiccek J. Tetrahedron Lett. 43 (2002) 2087-2090
165. Daly J.W., Brown G.B., Mensah-Dwumah M.M., and Meyers C.W. Toxicon 16 (1978) 163-188
166. Tokuyama T., Nishimori N., Karle I.K., Edwards M.W., and Daly J.W. Tetrahedron 42 (1986) 3453-3460
167. Smith III A.B., and Kim D.-S. Org. Lett. 6 (2004) 1493-1495
168. Oppolzer W., Flaskamp E., and Bieber L.W. Helv. Chim. Acta 84 (2001) 141-145
169. Oka T., Yasusa T., Ando T., Watanabe M., Yoneda F., Ishida T., and Knoll J. Bioorg. Med. Chem. 9 (2001) 1213-1219
170. Frantz D.E., Fässler R., and Carreira E.M. J. Am. Chem. Soc. 122 (2000) 1806-1807
171. Anand N.K., and Carreira E.M. J. Am. Chem. Soc. 123 (2001) 9687-9688
172. Jiang B., Chen Z., and Xiong W. Chem. Commun. (2002) 1524-1525
173. Satoh T., Imai T., Umeda S., Tsuda K., Hashimoto H., and Kakuchi T. Carbohydr. Res. 340 (2005) 2677-2681
174. Kamada M., Satoh T., Kakuchi T., and Yokota K. Tetrahedron: Asymmetry 10 (1999) 3667-3669
175. Quinoa E., Kakou Y., and Crews P. J. Org. Chem. 53 (1988) 3642-3644
176. Corley D.G., Herb R., Moore R.E., Scheuer P.J., and Paul V.J. J. Org. Chem. 53 (1988) 3644-3646
177. Jefford C.W., Bernardinelli G., Tanaka J.-I., and Higa T. Tetrahedron Lett. 37 (1996) 159-162
178. Mooberry S.L., Tien G., Hernandez A.H., Plubrukarn A., and Davidson B.S. Cancer Res. 59 (1999) 653-660
179. Dorling E.K., Öhler E., Mantoulidis A., and Mulzer J. Synlett (2001) 1105-1108
180. Ahmed A., Hoegenaur E.K., Enev V.S., Hanbauer M., Kaehlig H., Öhler E., and Mulzer J. J. Org. Chem. 68 (2003) 3026-3042
181. Catterall W.A. Science 242 (1988) 50-61 and references therein
182. Huang J.M.C., Wu H.C., and Baden D.G. J. Pharmacol. Exp. Ther. 229 (1984) 615-621
183. Yasumoto T., and Murata M. Chem. Rev. 93 (1993) 1897-1909 and references therein
184. Scheuer P.J. Tetrahedron 50 (1994) 3 and references therein
185. Bidard J.-N., Vijverberg H.P.M., Frelin C., Chungue E., Legrand A.-M., Bagnis R., and Lazdanski M. J. Biol. Chem. 259 (1984) 8353-8357
186. Lombet A., Bidard J.-N., and Lazdanski M. FEBS Lett. 219 (1987) 355-359
187. Holland J.M., Lewis M., and Nelson A. J. Org. Chem. 68 (2003) 747-753
188. Jiang S., Liu Z.-H., Sheng G., Zeng B.-B., Cheng X.-G., Wu Y.-L., and Yao Z.-J. J. Org. Chem. 67 (2002) 3404-3408
189. He Y.-T., Xue S., Hu T.-S., and Yao Z.-J. Tetrahedron Lett. 46 (2005) 5393-5397
190. Maezaki N., Tominaga H., Kojima N., Yanai M., Urabe D., Ueki R., Tanaka T., and Yamori T. Chem.-Eur. J. 11 (2005) 6237-6245
191. Wyatt P.B., and Blakskjaer P. Tetrahedron Lett. 40 (1999) 6481-6483
192. Tadeusiak E., Krawiecka B., and Michalski J. Tetrahedron Lett. 40 (1999) 1791-1792
193. Hemmi K., Takeno H., Hashimoto M., and Kamiya T. Chem. Pharm. Bull. 29 (1981) 646-650
194. Baer E., and Basu H. Can. J. Biochem. 47 (1969) 955-960
195. Wróblewski A.E., and Halajewska-Wosik A. Tetrahedron: Asymmetry 11 (2000) 2053-2055
196. Wróblewski A.E., and Halajewska-Wosik A. Eur. J. Org. Chem. (2002) 2758-2763
197. Jin C., Ramirez R.D., and Gopalan A.S. Tetrahedron Lett. 42 (2001) 4747-4750
198. Moolenaar W.H. Exp. Cell Res. 253 (1999) 230-238
199. Xu Y., Qian L., and Prestwich G.D. J. Org. Chem. 68 (2003) 5320-5330
200. Xu Y., and Prestwich G.D. Org. Lett. 4 (2002) 4021-4024
201. Rodriguez A.R., and Spur B.W. Tetrahedron Lett. 45 (2004) 8717-8720
202. Shoji J., Sakajaki R., Wakisaka Y., Koizumi K., Mayama M., and Matsurra S.J. J. Antibiot. 28 (1975) 122-125
203. Raghavan S., and Reddy S.R. J. Org. Chem. 68 (2003) 5754-5757
204. 3CN.
205. Cosse A.A., Bartelt R.J., James D.G., and Petroski R.J. J. Chem. Ecol. 27 (2001) 1841-1851
206. Mori K. Eur. J. Org. Chem. (2005) 2040-2044
207. Kolb H.C., and Sharpless K.B. Tetrahedron 48 (1992) 10515-10530
208. Chu M., Mierzwa R., Xu L., He L., Terracciano J., Patel M., Gullo V., Black T., Zhao W., Chan T.-M., and McPhail A.T. J. Nat. Prod. 66 (2003) 1527-1530
209. Jayasuriya H., Zink D.L., Polishook J.D., Bills G.F., Dombrowski A.W., Genilloud O., Pelaez F.F., Herranz L., Quamina D., Lingham R.B., Danzeizen R., Graham P.L., Tomassini J.E., and Singh S.B. Chem. Biodivers 2 (2005) 112-122
210. Snider B.B., and Zhou J. Org. Lett. 8 (2006) 1283-1286
211. Guard S., and Watson S.P. Neurochem. Int. 18 (1991) 149-165
212. For reviews, see
213. Takeuchi Y., Shands E.F.B., Beusen D.D., and Marshall G.R. J. Med. Chem. 41 (1998) 3609-3623
214. Maggi C.A., Patacchini R., Rovero P., and Giachetti A. J. Auton. Pharmacol. 13 (1993) 23-93
215. MacLean S. Med. Res. Rev. 16 (1996) 297-317
216. Owen, S. N.; Seward, E. M.; Swain, C. J.; Williams, B. J. U.S. Patent 6,458,830 B1, 2001.
217. Nelson T.D., Rosen J.D., Smitrovich J.H., Payack J., Craig B., Matty L., Huffman M.A., and McNamara J. Org. Lett. 7 (2005) 55-58
218. Bose D.S., Fatima L., and Rajender S. Synthesis (2006) 1863-1867
219. In: Ferrari R., Di Mauro S., and Sherwood G. (Eds). l-Carnitine and its Role in Medicine: From Function to Therapy (1992), Academic, San Diego
220. De Simone C., and Famularo G. Carnitine Today (1997), Springer, Heidelberg
221. Engel A.G. In: Frenkel R.A., and McGarry J.D. (Eds). Carnitine Biosynthesis Metabolism and Functions (1980), Academic, New York, NY 271
222. Hirata Y., and Uemura D. Pure Appl. Chem. 58 (1986) 701-710
223. Pettit G.R., Herald C.L., Boyd M.R., Leet J.E., Dufresne C., Doubek D.L., Schmidt J.M., Cerny R.L., Hooper J.N.A., and Rutzler K.C. J. Med. Chem. 34 (1991) 3339-3340
224. Bai R., Paull K.D., Herald C.L., Malspeis L., Pettit G.R., and Hamel E. J. Biol. Chem. 266 (1991) 15882-15889
225. Paull K.D., Lin C.M., Malspeis L., and Hamel E. Cancer Res. 52 (1992) 3892-3900
226. Pettit G.R. Pure Appl. Chem. 66 (1994) 2271-2281
227. Xie C., Nowak P., and Kishi Y. Org. Lett. 4 (2002) 4427-4429
228. Aicher T.D., Buszek K.R., Fang F.G., Forsyth C.J., Jung S.H., Kishi Y., Matelich M.C., Scola P.M., Spero D.M., and Yoon S.K. J. Am. Chem. Soc. 114 (1992) 3162-3164
229. Kishi Y. Pure Appl. Chem. 64 (1992) 343-350
230. Stamos D.P., Chen S.S., and Kishi Y. J. Org. Chem. 62 (1997) 7552-7553
231. Jin H., Uenishi J., Christ W.J., and Kishi Y. J. Am. Chem. Soc. 108 (1986) 5644-5646
232. Takai K., Tagashira M., Kuroda T., Oshima K., Utimoto K., and Nozaki H. J. Am. Chem. Soc. 108 (1986) 6048-6050
233. Larrow J.F., Schaus S.C., and Jacobsen E.N. J. Am. Chem. Soc. 118 (1996) 7420-7421
234. For preparation of 9-[2-(hydroxypropyl)]adenine, see:. Schaeffer H.J., and Vince R. J. Med. Chem. 10 (1967) 689-691
235. For similar phosphonomethoxytosylate alkylation reaction, see:. Yu K.-L., Bronson J.J., Yang H., Patick A., Alam M., Brankovan V., Datema R., Hitchcock M.J.M., and Martin J.C. J. Med. Chem. 35 (1992) 2958-2969
236. Singleton V.L., Bohonos N., and Ullstrup A.J. Nature (London) 181 (1958) 1072-1073
237. Betina V., Betinova M., and Kutkova M. Arch. Mikrobiol. 55 (1966) 1-16
238. Takatsuki A., Yamaguchi I., Tamura G., Misato T., and Amrima K. J. Antibiot. 22 (1969) 442-445
239. Betina V. Neoplasma 16 (1969) 23-32
240. Bacikova D., Betina V., and Nemec P. Naturwissenschaften 51 (1964) 445-446
241. Wu Y., Shen X., Yang Y.-Q., Hu Q., and Huang J.-H. Tetrahedron Lett. 45 (2004) 199-202
242. Pettit G.R., Day J.F., Hartwell J.L., and Wood H.B. Nature 227 (1970) 962-963
243. Wender P.A., Cribbs C.M., Koehler K.F., Sharkey N.A., Herald C.L., Kamano Y., Pettit G.R., and Blumberg P.M. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 7197-7201
244. Pettit G.R. Progress in the Chemistry of Organic Natural Products Vol. 57 (1991), Springer, New York, NY pp 153-195
245. Yadav J.S., Bandyopadhyay A., and Kunwar A.C. Tetrahedron Lett. 42 (2001) 4907-4911
246. Yadav J.S., and Srihari P. Tetrahedron: Asymmetry 15 (2004) 81-89
247. Tsuda M., Hirano K., Kubota T., and Kobayashi J. Tetrahedron Lett. 40 (1999) 4819-4820
248. Romeril S.P., Lee V., Baldwin J.E., Claridg T.D.W., and Odell B. Tetrahedron Lett. 44 (2003) 7757-7761
249. Kulkarni B.A., Roth G.P., Lobkovsky E., and Porco Jr. J.A. J. Comb. Chem. 4 (2002) 56-72
250. Stob M., Baldwin R.S., Tuite J., Andrews F.N., and Gillette K.G. Nature 196 (1962) 1318-1319
251. Fürstner A., Thiel O.R., Kindler N., and Bartkowska B. J. Org. Chem. 65 (2000) 7990-7995
252. Mayers A.G., and Lanman B.A. J. Am. Chem. Soc. 124 (2002) 12969-12971
253. Lanman B.A., and Myers A.G. Org. Lett. 6 (2004) 1045-1047