Total syntheses of amphidinolide X and Y

Journal of the American Chemical Society

Volumn 128, Issue 28, 2006, Pages 9194-9204

  Fürstner, Alois ^a   Kattnig, Egmont ^a   Lepaqe, Olivier ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; IRON; METABOLITES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALLENOL; AMPHIDINOLIDE; GRIGNARD REAGENT; SYN-SELECTIVE FORMATION;

ALCOHOLS;

19 EPI AMPHIDINOLIDE; ALDEHYDE; ALLENOL; AMPHIDINOLIDE X; AMPHIDINOLIDE Y; CYTOTOXIC AGENT; MAGNESIUM BROMIDE; METHYL GROUP; NATURAL PRODUCT; PALLADIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHIRALITY; CYCLIZATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; ECONOMIC ASPECT; ENANTIOMER; ESTERIFICATION; HYDROGENATION; IRON KINETICS; MARINE ENVIRONMENT; METABOLITE; METHODOLOGY; OXIDATION KINETICS; PROMOTER REGION; RING OPENING; STEREOCHEMISTRY; SUZUKI REACTION;

BIOLOGICAL PRODUCTS; MACROLIDES; MOLECULAR STRUCTURE;

EID: 33746066374     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061918e     Document Type: Article

References (154)

1. (a) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77.
2. (b) Ishibashi, M.; Kobayashi, J. Heterocycles 1997, 44, 543.
3. (c) Chakraborty, T. K.; Das, S. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 131.
4. (d) Kobayashi, J.; Ishibashi, M. In Comprehensive Natural Products Chemistry; Mori, K., Ed.; Elsevier: Amsterdam, 1999; Vol. 8; pp 415-649.
5. 50 values as low as 0.00014 μg/mL were reported: hence, amphidinolides H and N exhibit potencies similar to that of the spongistatins, cf. ref 1.
6. (a) Review: Rein, K. S.; Borrone, J. Camp. Biochem. Physiol., B 1999, 124, 117.
7. (b) For representative studies on the biosynthesis of the amphidinolides see: Kobayashi, J.; Takahashi, M.; Ishibashi, M. J. Chem. Soc., Chem. Commun. 1995, 1639.
8. (c) Ishibashi, M.; Takahashi, M.; Kobayashi, J. Tetrahedron 1997, 53, 7827.
9. (d) Sato, M.; Shimbo, K.; Tsuda, M.; Kobayashi, J. Tetrahedron Lett. 2000, 41, 503.
10. Tsuda, M.; Izui, N.; Shimbo, K.; Sato, M.; Fukushi, E.; Kawabata, J.; Katsumata, K.; Horiguchi, T.; Kobayashi, J. J. Org. Chem. 2003, 68, 5339.
11. For a recent review on macrodiolides see: Kang, E. J.; Lee, E. Chem. Rev. 2005, 105, 4348.
12. Tsuda, M.; Izui, N.; Shimbo, K.; Sato, M.; Fukushi, E.; Kawabata, J.; Kobayashi, J. J. Org. Chem. 2003, 68, 9109.
13. Recent examples: (a) Fürstner, A.; Domostoj, M. M.; Scheiper, B. J. Am. Chem. Soc. 2005, 127, 11620.
14. (b) Fürstner, A.; Turet, L. Angew. Chem., Int. Ed. 2005, 44, 3462.
15. (c) Fürstner, A.; Radkowski, K.; Peters, H. Angew. Chem., Int. Ed. 2005, 44, 2777.
16. (d) Scheiper, B.; Glorius, F.; Leitner, A.; F̈rstner, A. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11960.
17. (e) Fürstner, A.; Jeanjean, F.; Razon, P. Angew. Chem., Int. Ed. 2002, 41, 2097.
18. (f) Fürstner, A.; Müller, C. Chem. Commun. 2005, 5583.
19. (g) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061.
20. (h) Fürstner, A.; Mamane, V. Chem. Commun. 2003, 2112.
21. (i) Fürstner, A.; Wuchrer, M. Chem. Eur. J. 2006, 12, 76.
22. (j) Fürstner, A.; Hannen, P. Chem. Eur. J. 2006, 12, 3006.
23. (a) Fürstner, A.; Kirk, D.; Fenster, M. D. B.; Aïssa, C.; De Souza, D.; Müller, O. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 8103.
24. (b) Fürstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582.
25. (c) Fürstner, A. Eur. J. Org. Chem. 2004, 943.
26. (d) Fürstner, A.; Feyen, F.; Prinz, H.; Waldmann, H. Tetrahedron 2004, 60, 9543.
27. (a) Aïssa, C.; Riveiros, R.; Ragot, J.; Fürstner, A. J. Am. Chem. Soc. 2003, 125, 15512.
28. (b) Fürstner, A.; Aïssa, C.; Riveiros, R.; Ragot, J. Angew. Chem., Int. Ed. 2002, 41, 4763.
29. For total syntheses of amphidinolides reported by other groups, see: (a) Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198.
30. (b) Williams, D. R.; Myers, B. J.; Mi, L. Org. Lett. 2000, 2, 945.
31. (c) Williams, D. R.; Meyer, K. G. J. Am. Chem. Soc. 2001, 123, 765.
32. (d) Lam, H. W.; Pattenden, G. Angew. Chem., Int. Ed. 2002, 41, 508.
33. (e) Maleczka, R. E., Jr.; Terrell, L. R.; Geng, F.; Ward, J. S. Org. Lett. 2002, 4, 2841.
34. (f) Ghosh, A. K.; Liu, C. J. Am. Chem. Soc. 2003, 125, 2374.
35. (g) Trost, B. M.; Harrington, P. E. J. Am. Chem. Soc. 2004, 126, 5028.
36. (h) Ghosh, A. K.; Gone, G. J. Am. Chem. Soc. 2004, 126, 3704.
37. (i) Colby, E. A.; O'Brien, K. C.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 998.
38. (j) Trost, B. M.; Papillon, J. P. N. J. Am. Chem. Soc. 2004, 126, 13618.
39. (k) Trost, B. M.; Chisholm, J. D.; Wrobleski, S. T.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420.
40. (l) Ghosh, A. K.; Gong, G. J. Org. Chem. 2006, 71, 1085.
41. Trost, B. M.; Papillon, J. P. N.; Nussbaumer, T. J. Am. Chem. Soc. 2005, 127, 17921.
42. (n) Trost, B. M.; Harrington, P. E.; Chisholm, J. D.; Wrobleski, S. T. J. Am. Chem. Soc. 2005, 127, 13598.
43. (o) Colby, E. A.; Jamison, T. F. Org. Biomol. Chem. 2005, 3, 2675.
44. (p) Colby, E. A.; O'Brien, K. C.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 4297.
45. Preliminary communication: Lepage, O.; Kattnig, E.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 15970.
46. For a discussion see: Fürstner, A. Synlett 1999, 1523.
47. Fürstner, A.; Méndez, M. Angew. Chem., Int. Ed. 2003, 42, 5355.
48. (a) Fürstner, A.; Martin, R. Chem. Lett. 2005, 34, 624.
49. (b) See also: Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
50. (c) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955.
51. (d) Scheiper, B.; Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3943.
52. (e) Seidel, G.; Laurich, D.; Fürstner, A. J. Org. Chem. 2004, 69, 3950.
53. (f) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609.
54. (g) Fürstner, A.; Martin, R.; Majima, K. J. Am. Chem. Soc. 2005, 127, 12236.
55. (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
56. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
57. (c) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
58. (d) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
59. Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8.
60. (a) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204.
61. (b) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236.
62. Wang, Z.-X.; Cao, G.-A.; Shi, Y. J. Org. Chem. 1999, 64, 7646.
63. Nacro, K.; Baltas, M.; Gorrichon, L. Tetrahedron 1999, 55, 14013.
64. Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 231-280.
65. (a) Ohira, S. Synth. Commun. 1989, 19, 561.
66. (b) Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521.
67. Marshall, J. A.; Pinney, K. G. J. Org. Chem. 1993, 58, 7180.
68. Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Eur. J. Org. Chem. 1998, 1675.
69. Originally, it had been envisaged to install the missing -OH group at C. 17 via hydroboration/oxidation or, alternatively, by a Wacker oxidation of the olefin in 19 followed by reduction of the resulting ketone; however, both sequences turned out to be unsatisfactory.
70. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
71. For a recent alternative synthesis of a D-synthon surrogate see: Chen, Y.; Jin, J.; Wu, J.; Dai, W.-M., Synlett 2006, 1177.
72. Toluene should not be used as substitute for benzene in the acetalization reaction because the separation of the volatile product is then much more difficult and results in significantly lower yields.
73. The literature reports that this Dibal-H reduction affords the corresponding alcohol, cf: Langer, P.; Freifeld, I. Synlett 2001, 523; in our hands, however, the reduction reproducibly stopped at the aldehyde stage even if an excess Dibal-H was used.
74. (a) Marshall, J. A. Chem. Rev. 2000, 100, 3163.
75. (b) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1999, 64, 5201.
76. (c) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2001, 66, 7825.
77. For a recent application see: Beşev, M.; Brehm, C.; Fürstner, A. Collect. Czech. Chem. Commun. 2005, 70, 1696.
78. (a) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
79. (b) Hart, D. W.; Schwartz, J. J. Am. Chem. Soc. 1974, 96, 8115
80. Hu, T.; Panek, J. S. J. Am. Chem. Soc. 2002, 124, 11368.
81. 3 once the color of iodine starts to persist in order to ensure high and reproducible yields, cf. Supporting Information.
82. Bode, J. W.; Carreira, E. M. J. Org. Chem. 2001, 66, 6410.
83. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
84. (a) Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
85. (b) Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175.
86. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399.
87. Such a transformation could be achieved via zinc insertion into the C-X bond in the AD fragment followed by Negishi cross coupling. Exploratory studies, however, invariably resulted in low yields and were abandoned in favor of the Suzuki route.
88. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
89. (a) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
90. (b) Hikota, M.; Sakurai, Y.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1990, 31, 6367.
91. (a) Review: Parenty, A.; Moreau, X.; Campagne, J.-M. Chem. Rev. 2006, 106, 911.
92. (b) For a recent application from this laboratory, see: Mlynarski, J.; Ruiz-Caro, J.; Fürstner, A. Chem. Eur. J. 2004, 10, 2214.
93. (a) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165.
94. (b) Fürstner, A.; Leitner, A. Synlett 2001, 290.
95. (c) Fürstner, A.; Nikolakis, K. Liebigs Ann. 1996, 2107.
96. (d) Fürstner, A.; Seidel, G. Synlett 1998, 161.
97. (e) The method was also independently reported by: Soderquist, J. A.; Matos, K.; Rane, A.; Ramos, J. Tetrahedron Lett. 1995, 36, 2401.
98. For general reviews on the Suzuki reaction see, inter alia: (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
99. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
100. (a) Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
101. (b) Mickel, S. J. et al. Org. Process Res. Dev. 2004, 8, 113-121.
102. (c) Yuan, Y.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 14720.
103. Reviews on the alkyl-Suzuki reaction and applications to total synthesis: (a) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
104. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
105. (c) For early applications of the alkyl-Suzuki reaction from this laboratory, see: Fürstner, A.; Konetzki, I. J. Org. Chem. 1998, 63, 3072.
106. (d) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071.
107. (e) Fürstner. A.; Seidel, G. J. Org. Chem. 1997, 62, 2332.
108. (f) Fürstner, A.; Seidel, G.; Gabor, B.; Kopiske, C.; Krüger, C.; Mynott, R. Tetrahedron 1995, 51, 8875.
109. Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2002, 4, 4447.
110. For other macrodiolide syntheses from this laboratory see: (a) Fürstner, A.; Albert, M.; Mlynarski, J.; Matheu, M.; DeClercq, E. J. Am. Chem. Soc. 2003, 125, 13132.
111. (b) Fürstner, A.; Ruiz-Caro, J.; Prinz, H.; Waldmann, H. J. Org. Chem. 2004, 69, 459.
112. (c) Fürstner, A.; Thiel, O. R.; Ackermann, L. Org. Lett. 2001, 3, 449.
113. (d) Fürstner, A.; Mlynarski, J.; Alben, M. J. Am. Chem. Soc. 2002, 124, 10274.
114. (e) Fürstner, A.; Albert, M.; Mlynarski, J.; Matheu, M. J. Am. Chem. Soc. 2002, 124, 1168.
115. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769.
116. The enantiomer of 52 is known, see: Organ, M. G.; Wang, J. J. Org. Chem. 2003, 68, 5568.
117. Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc., Perkin Trans. 1 1981, 2527.
118. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
119. (b) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
120. (c) Boeckman, R. K., Jr.; Shao, P.; Mullins, J. J. Org. Synth. 2000, 77, 141.
121. Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348.
122. (a) Nakamura, E. Tetrahedron Lett. 1981, 22, 663.
123. (b) Schmidt, U.; Langner, J.; Kirschbaum, B.; Braun, C. Synthesis 1994, 1138.
124. Reviews: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
125. (b) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin. 1999; Vol. 1; pp 199-246.
126. (c) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
127. (d) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
128. For precedence on enantioselective hydrogenations of α-ketoesters with Ru-based catalysts, see the following for leading references and literature cited therein: (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
129. (b) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.
130. (c) Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genêt, J. P.; Champion, N.; Dellis, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5799.
131. (d) Benincori, T.; Piccolo, O.; Rizzo, S.; Sannicolò, F. J. Org. Chem. 2000, 65, 8340.
132. (e) Transfer hydrogenation: Šterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Lett. 2004, 45, 535.
133. The catalyst was prepared as described in: King, S. A.; Keller, J. Org. Synth. 2005, 81, 178.
134. For precedence on the diastereoselective hydrogenation of a chiral α-ketoester see: Gao, Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133.
135. (a) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. J. Am. Chem. Soc. 1999, 121, 7540. To the best of our knowledge, this is the only report showing 1.4-induction by α-alkoxy substitutents in methyl ketones without any superimposed 1,5-induction and/or directing effects exerted by substituents in the aldehyde component.
136. For further examples in which such effects might be operative in addition to 1,4-induction see: (b) Crimmins, M. T.; Katz, J. D.; McAtee, L. C.; Tabet, E. A.; Kirincich, S. J. Org. Lett. 2001, 3, 949.
137. (c) Paterson, I.; Coster, M. J.; Chen, D. Y.-K.; Aceña, J. L.; Bach, J.; Keown, L. E.; Trieselmann, T. Org. Biomol. Chem. 2005, 3, 2420.
138. For pertinent discussions on the related 1.5-induction observed in reactions of β-alkoxy substituted methyl ketone enolates with (chiral) aldehydes see the following for leading references: (a) Gustin, D. J.; VanNieuwenhze, M. S.; Roush, W. R. Tetrahedron Lett. 1995, 36, 3443.
139. (b) Evans, D. A.; Côté, B.; Coleman, P. J.; Connell, B. T. J. Am. Chem. Soc. 2003, 125, 10893.
140. (c) Paterson, I.; Collett, L. A. Tetrahedron Lett. 2001, 42, 1187.
141. (d) Roush, W. R.; Bannister, T. D.; Wendt, M. D.; Jablonowski, J. A.; Scheidt, K. A. J. Org. Chem. 2002, 67, 4275 and literature cited therein.
142. Review: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
143. (a) Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663.
144. (b) Ramachandran, P. V.; Xu, W.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4911.
145. For precedence see: Bhattacharjee, A.; Soltani, O.; De Brabander, J. K. Org. Lett. 2002, 4, 481.
146. Evans, D. A.; Dart, M. J.; Duffy. J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322.
147. Reetz, M. T. Acc. Chem. Res. 1993, 26, 462.
148. For pertinent examples in the ketone (rather than much more closely investigated aldehyde series) see: (a) "chelate controlled" MeMgI addition to α-alkoxyketone: Nakamura, S.; Inagaki, J.; Sugimoto, T.; Kudo, M.; Nakajima, M.; Hashimoto, S. Org. Lett. 2001, 3, 4075.
149. (b) "Dipole controlled" addition of MeMgBr to β-silyloxy ketones: Ukaji, Y.; Kanda, H.; Yamamoto, K.; Fujisawa, T. Chem. Lett. 1990, 19, 591.
150. For a related example see: Trost, B. M.; Ball, Z. T.; Laemmerhold, K. M. J. Am. Chem. Soc. 2005, 127, 10028.
151. Stamos, D. P.; Taylor, A. G.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8647.
152. Note that this spontaneous cyclization provides further evidence for the cis-orientation of the alkyl group at the anomeric center and the tertiary alcohol group generated through chelate-Cram addition.
153. + salts formed as byproducts in the generation of the mixed anhydride are filtered off prior to concentration of the solution and subsequent macrocyclization. This protocol is highly advisable for very acid-sensitive compounds, cf: Evans, D. A.; Connell, B. T. J. Am. Chem. Soc. 2003, 125, 10899.
154. Unprotected samples of the crude seco-acid were obtained by lowering the pH during the extractive work to <5.