High stereochemical diversity and applications for the synthesis of marine natural products: A library of carbohydrate mimics and polyketide segments

Chemistry - A European Journal

Volumn 6, Issue 18, 2000, Pages 3313-3320

  Misske, Andrea M ^a,b   Hoffmann, H Martin R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b BASF SE   (Germany)

Author keywords

Aldol reactions; Biodiversity; Carbohydrate; Combinatorial chemistry; Polyketides

Indexed keywords

2,4 DIMETHYL 8 OXABICYCLO[3.2.1]OCT 6 EN 3 ONE; ACETAL DERIVATIVE; CARBOHYDRATE DERIVATIVE; NATURAL PRODUCT; POLYKETIDE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIODIVERSITY; CARBOHYDRATE SYNTHESIS; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034665454     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0     Document Type: Short Survey

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41. Total syntheses: g) D. A. Evans, P. J. Coleman, L. C. Diaz, Angew. Chem. 1997, 109, 2951 ; Angew. Chem. Int. Ed. 1997, 36, 2737; D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, Angew. Chem. 1997, 109, 2954; Angew. Chem. Int. Ed. 1997, 36, 2741; D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Diaz, A. N. Tyler, Angew. Chem. 1997, 109, 2957; Angew. Chem. Int. Ed. 1997, 36, 2744 (Spongistatin 2);
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43. Total syntheses: g) D. A. Evans, P. J. Coleman, L. C. Diaz, Angew. Chem. 1997, 109, 2951 ; Angew. Chem. Int. Ed. 1997, 36, 2737; D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, Angew. Chem. 1997, 109, 2954; Angew. Chem. Int. Ed. 1997, 36, 2741; D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Diaz, A. N. Tyler, Angew. Chem. 1997, 109, 2957; Angew. Chem. Int. Ed. 1997, 36, 2744 (Spongistatin 2);
44. Total syntheses: g) D. A. Evans, P. J. Coleman, L. C. Diaz, Angew. Chem. 1997, 109, 2951 ; Angew. Chem. Int. Ed. 1997, 36, 2737; D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, Angew. Chem. 1997, 109, 2954; Angew. Chem. Int. Ed. 1997, 36, 2741; D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Diaz, A. N. Tyler, Angew. Chem. 1997, 109, 2957; Angew. Chem. Int. Ed. 1997, 36, 2744 (Spongistatin 2);
45. h) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198; Angew. Chem. Int. Ed. 1998, 37, 187; M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202; Angew. Chem. Int. Ed. 1998, 37, 190 (Spongistatin 1).
46. h) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198; Angew. Chem. Int. Ed. 1998, 37, 187; M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202; Angew. Chem. Int. Ed. 1998, 37, 190 (Spongistatin 1).
47. h) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198; Angew. Chem. Int. Ed. 1998, 37, 187; M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202; Angew. Chem. Int. Ed. 1998, 37, 190 (Spongistatin 1).
48. h) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198; Angew. Chem. Int. Ed. 1998, 37, 187; M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202; Angew. Chem. Int. Ed. 1998, 37, 190 (Spongistatin 1).
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89. q) ref. [3];
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107. n) G. Yang, D. C. Myles, Tetrahedron Lett. 1994, 35, 2503;
108. o) I. Paterson, A. Schlapbach, Synlett, 1995, 498;
109. p) J. A. Marshall, Z.-H. Lu, B. A. Johns, J. Org. Chem. 1998, 63, 817;
110. q)ref. [3];
111. r) see also A. B. Smith III, M. D. Kaufman, T. J. Beauchamp, M. J. LaMarche, H. Arimoto, Org. Lett. 1999, 1, 1823.
112. Structure elucidation and biological activity: a) J. W. Kim, H. Adachi, K. Shin-ya, Y. Hayakawa, H. Seto, J. Antibiot. 1997, 50, 628;
113. b) Y. Hayakawa, J. W. Kim, H. Adachi, K. Shin-ya, K. Fujita, H. Seto, J. Am. Chem. Soc. 1998, 120, 3524.
114. Synthetic effort: c) J. Schuppan, B. Ziemer, U. Koert, Tetrahedron Lett. 2000, 41, 621.
115. a) O. Gaertzen, A. M. Misske, P. Wolbers, H. M. R. Hoffmann, Synlett 1999, 1041;
116. b) O. Gaertzen, A. M. Misske, P. Wolbers, H. M. R. Hoffmann, Tetrahedron Lett. 1999, 40, 6359.
117. The conformation was confirmed by a 500 MHz NOESY spectrum.
118. a) D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155;
119. b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277; J. A. Marshall, G. P. Luke, J. Org. Chem. 1993, 58, 6229.
120. b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277; J. A. Marshall, G. P. Luke, J. Org. Chem. 1993, 58, 6229.
121. S. Trippett, D. M. Walker, J. Chem. Soc. 1959, 3874.
122. + 327.1834, found 327.1834.
123. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
124. + 306.1467, found 306.1467.
125. a) P. C. Bulman Page, M. B. van Niel, J. C. Prodger, Tetrahedron 1989, 45, 7643;
126. b) M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192; Angew. Chem. Int. Ed. 1996, 35, 2056.
127. b) M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192; Angew. Chem. Int. Ed. 1996, 35, 2056.
128. M. Kassou, S. Castillón, J. Org. Chem. 1997, 62, 3696.
129. + 589.3169, found 589.3171.
130. Structure elucidation: a) G. R. Pettit, Progr. Chem. Org. Nat. Prod. 1991, 57, 153;
131. b) G. R. Pettit, J. Nat. Prod. 1996, 59, 812.
132. Total synthesis of bryostatin 7: c) M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407.
133. Total synthesis of bryostatin 2: d) D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, M. Lautens, J. Am. Chem. Soc. 1999, 121, 7540;
134. e) D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, M. Lautens, Angew. Chem. 1998, 110, 2526; Angew. Chem. Int. Ed. 1998, 37, 2354.
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136. Review: f) R. D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041.
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151. u) S. Kiyooka, H. Maeda, Tetrahedron: Asymmetry 1997, 8, 3371;
152. v) J. M. Weiss, H. M. R. Hoffmann, Tetrahedron: Asymmetry 1997, 8, 3913;
153. w) J. DeBrabander, B. A. Kulkarni, R. Garcia-Lopez, M. Vandewalle, Tetrahedron: Asymmetry 1997, 8, 1721;
154. x) J. Gracia, E. J. Thomas, J. Chem. Soc. Perkin Trans. I 1998, 17, 2865;
155. y) R. J. Maguire, S. P. Munt, E. J. Thomas, J. Chem. Soc. Perkin Trans. I 1998, 17, 2853;
156. z) J. Baxter, E. G. Mate, E. J. Thomas, Tetrahedron 1998, 54, 14359;
157. aa) T. Obitu, K. Ohmori, Y. Ogawa, H. Hosomi, S. Ohba, S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1998, 39, 7349.
158. Structure elucidation: A. Furusaki, T. Watanabe, T. Matsumoto, M. Yanagiya, Tetrahedron Lett. 1968, 6301.
159. Review on structure elucidation and biological activity of pederin: b) J. H. Frank, K. Kanamitsu, Med. Entomol. 1987, 24, 155.
160. Total syntheses: c) F. Matsuda, N. Tomiyoshi, M. Yanagiya, T. Matsumoto, Tetrahedron 1988, 44, 7063;
161. d) T. Nakata, S. Nagao, N. Mori, T. Oishi, Tetrahedron Lett. 1985, 26, 6461;
162. e) T. Nakata, S. Nagao, T. Oishi, Tetrahedron Lett. 1985, 26, 6465;
163. f) T. M. Wilson, P. Kocienski, K. Jarowicki, K. Isaac, P. M. Hitchcock, A. Faller, S. F. Campbell, Tetrahedron 1990, 46, 1767;
164. g) P. Kocienski, K. Jarowicki, S. Marczak, Synthesis 1991, 1191.
165. Other synthetic efforts: h) J. Meinwald, Pure Appl. Chem. 1977, 49, 1275;
166. i) M. C. Pirrung, P. M. Kenney, J. Org. Chem. 1987, 52, 2335;
167. j) A. Vakalopoulos, H. M. R. Hoffmann, unpublished results.
168. Isolation and structural work: a) P. A. Horton, F. E. Koehn, R. E. Longley, O. J. McConnell, J. Am. Chem. Soc. 1994, 116, 6015.
169. Synthetic efforts: b) H. Beck, H. M. R. Hoffmann, Eur. J. Org. Chem. 1999, 2991;
170. c) M. Nowakowski, H. M. R. Hoffmann, Tetrahedron 1997, 53, 4331.
171. a) K. Gerth, H. Schummer, G. Höfle, H. Irschik, H. Reichenbach, J. Antibiot. 1995, 48, 787;
172. b) D. Schummer, K. Gerth, H. Reichenbach, G. Höfle, Liebigs Ann. 1995, 685;
173. c) P. M. Schäfer, H. M. R. Hoffmann, unpublished results.
174. T. Higa, J. Tanaka, M. Komesu, D. G. Gravalos, J. L. F. Puentes, G. Bernardinelli, C. W. Jefford, J. Am. Chem. Soc. 1992, 114, 7587.
175. For further syntheses of P-, S-, and NC-pseudoglycosides see R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385.
176. Truly combinatorial biosynthesis has probably not yet arrived. For the study of polyketide segment synthases (PKS) see: a) J. Staunton, B. Wilkinson, Chem. Rev. 1997, 97, 2611;
177. b) D. A. Hopwood, Chem. Rev. 1997, 97, 2465;
178. c) C. Khosla, Chem. Rev. 1997, 97, 2577;
179. d) R. L. Rawls, Chem. Eng. News 1998, March 9, 29.
180. See also H. M. R. Hoffmann, Encyclopedia of Reagents for Organic Synthesis, Vol. 7 (Ed.: L. A. Paquette), Wiley, Chichester, 1995, 4591; M. R. Ashcroft, H. M. R. Hoffmann, Org. Synth. Coll. Vol. 6, 1988, p. 512.
181. See also H. M. R. Hoffmann, Encyclopedia of Reagents for Organic Synthesis, Vol. 7 (Ed.: L. A. Paquette), Wiley, Chichester, 1995, 4591; M. R. Ashcroft, H. M. R. Hoffmann, Org. Synth. Coll. Vol. 6, 1988, p. 512.