Stereoselective total synthesis of reveromycin B and C19-epi-reveromycin B

Chemistry - A European Journal

Volumn 6, Issue 11, 2000, Pages 1987-2001

  Drouet, Keith E ^a   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Natural products; Reveromycin; Synthetic methods; Total synthesis

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; NATURAL PRODUCT; PYRAN DERIVATIVE; REVEROMYCIN B; REVEROMYCIN B DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMISTRY; DRUG POTENCY; DRUG SYNTHESIS; REACTION ANALYSIS; SPECTROSCOPY; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTIBIOTICS, ANTINEOPLASTIC; PYRANS; SPECTRUM ANALYSIS; SPIRO COMPOUNDS; STEREOISOMERISM; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, NON-P.H.S.;

EID: 0034596069     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000602)6:11<1987::AID-CHEM1987>3.0.CO;2-U     Document Type: Article

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36. For selected references on the Kishi-Nozaki (Nozaki-Hiyama-Kishi) reaction see: a) A. Fürstner, N. Shi, J. Am. Chem. Soc. 1996, 118, 2533-2534; b) P. Cintas, Synthesis 1992, 248-257; c) H. Jin, J. Uenishi, W. J. Christ, Y. Kishi, J. Am. Chem. Soc. 1986, 108, 5644-5646; d) P. Wipf, S. Lim, J. Chem. Soc. Chem. Commun. 1993, 1654-1656; e) K. Takai, M. Tagashira, T. Kuroda, K. Oshima, K. Utimoto, H. Nozaki, J. Am. Chem. Soc. 1986, 108, 6048-6050; f) Y. Kishi, Pure Appl. Chem. 1992, 64, 343-350; g) Y. Kishi, Pure Appl. Chem. 1989, 61, 313-324; h) C. Chen, K. Tagami, Y. Kishi, J. Org. Chem. 1995, 60, 5386-5387; i) A. Fürstner, N. Shi, J. Am. Chem. Soc. 1996, 118, 12349-12357.
37. For selected references on the Kishi-Nozaki (Nozaki-Hiyama-Kishi) reaction see: a) A. Fürstner, N. Shi, J. Am. Chem. Soc. 1996, 118, 2533-2534; b) P. Cintas, Synthesis 1992, 248-257; c) H. Jin, J. Uenishi, W. J. Christ, Y. Kishi, J. Am. Chem. Soc. 1986, 108, 5644-5646; d) P. Wipf, S. Lim, J. Chem. Soc. Chem. Commun. 1993, 1654-1656; e) K. Takai, M. Tagashira, T. Kuroda, K. Oshima, K. Utimoto, H. Nozaki, J. Am. Chem. Soc. 1986, 108, 6048-6050; f) Y. Kishi, Pure Appl. Chem. 1992, 64, 343-350; g) Y. Kishi, Pure Appl. Chem. 1989, 61, 313-324; h) C. Chen, K. Tagami, Y. Kishi, J. Org. Chem. 1995, 60, 5386-5387; i) A. Fürstner, N. Shi, J. Am. Chem. Soc. 1996, 118, 12349-12357.
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81. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
82. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
83. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
84. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
85. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
86. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
87. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
88. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
89. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
90. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
91. For selected impressive examples on the use of Stille coupling in natural products synthesis see: a) M. B. Andrus, S. D. Lepore, J. Am. Chem. Soc. 1997, 119, 2327-2328; b) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095-13096; c) D. A. Evans, J. S. Johnson, J. Org. Chem. 1997, 62, 786-787; d) A. B. Smith III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1997, 119, 10935-10946; e) K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa, P. Bertinato, J. Am. Chem. Soc. 1993, 115, 4419-4420; f) K. C. Nicolaou, N. Winssinger, J. Pastor, F. Murphy, Angew. Chem. 1998, 110, 2677-2680; Angew. Chem. Int. Ed. 1998, 37, 2534-2537; g) T. M Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3164-3166; Angew. Chem. Int. Ed. 1998, 37, 2993-2995; h) T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168; Angew. Chem. Int. Ed. 1998, 37, 2995-2998.
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97. For selected recent synthetic applications of Negishi coupling see: a) B. H. Lipshutz, C. Lindsey, J. Am. Chem. Soc. 1997, 119, 4555-4556; b) A. Palmgren, A. Thorarensen, J. E. Backvall, J. Org. Chem. 1998, 63, 3764-3768; c) G. Boche, M. Klein, Synthesis 1999, 1246-1250; d) M. Jorgensen, M. Larsen, J. Org. Chem. 1997, 62, 4171-4173.
98. For selected recent synthetic applications of Negishi coupling see: a) B. H. Lipshutz, C. Lindsey, J. Am. Chem. Soc. 1997, 119, 4555-4556; b) A. Palmgren, A. Thorarensen, J. E. Backvall, J. Org. Chem. 1998, 63, 3764-3768; c) G. Boche, M. Klein, Synthesis 1999, 1246-1250; d) M. Jorgensen, M. Larsen, J. Org. Chem. 1997, 62, 4171-4173.
99. For selected recent synthetic applications of Negishi coupling see: a) B. H. Lipshutz, C. Lindsey, J. Am. Chem. Soc. 1997, 119, 4555-4556; b) A. Palmgren, A. Thorarensen, J. E. Backvall, J. Org. Chem. 1998, 63, 3764-3768; c) G. Boche, M. Klein, Synthesis 1999, 1246-1250; d) M. Jorgensen, M. Larsen, J. Org. Chem. 1997, 62, 4171-4173.
100. For selected recent synthetic applications of Negishi coupling see: a) B. H. Lipshutz, C. Lindsey, J. Am. Chem. Soc. 1997, 119, 4555-4556; b) A. Palmgren, A. Thorarensen, J. E. Backvall, J. Org. Chem. 1998, 63, 3764-3768; c) G. Boche, M. Klein, Synthesis 1999, 1246-1250; d) M. Jorgensen, M. Larsen, J. Org. Chem. 1997, 62, 4171-4173.
101. a) J. S. Panek, T. Hu, J. Org. Chem. 1997, 62, 4912-4913;
102. b) J. S. Panek, T. Hu, J. Org. Chem. 1997, 62, 4914-4915;
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104. For alternative, yet more tedious, approaches to this type of conjugated dienes see: a) A. R. de Lera, A. Torrado, B. Inglesias, S. Lopez, Tetrahedron Lett. 1992, 33, 6205-6208; b) J. P. Genet, A. Linquist, E. Blart, V. Mouries, M. Savignac, M. Vaultier, Tetrahedron Lett. 1995, 36, 1443-1446.
105. For alternative, yet more tedious, approaches to this type of conjugated dienes see: a) A. R. de Lera, A. Torrado, B. Inglesias, S. Lopez, Tetrahedron Lett. 1992, 33, 6205-6208; b) J. P. Genet, A. Linquist, E. Blart, V. Mouries, M. Savignac, M. Vaultier, Tetrahedron Lett. 1995, 36, 1443-1446.
106. For recent impressive demonstrations of the application of the Kishi-Nozaki coupling to natural products synthesis see: a) J. A. McCauley, K. Nagasawa, P. A. Lander, S. G. Mischke, M. A. Semones, Y. Kishi, J. Am. Chem. Soc. 1998, 120, 7647-7648; b) X.-T. Chen, S. K. Bhattacharya, B. Zhou, C. E. Gutteridge, T. R. R. Pettus, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 6563-6579; c) M. M. Victor, R. A. Pilli, Tetrahedron Lett. 1998, 39, 4421-4424.
107. For recent impressive demonstrations of the application of the Kishi-Nozaki coupling to natural products synthesis see: a) J. A. McCauley, K. Nagasawa, P. A. Lander, S. G. Mischke, M. A. Semones, Y. Kishi, J. Am. Chem. Soc. 1998, 120, 7647-7648; b) X.-T. Chen, S. K. Bhattacharya, B. Zhou, C. E. Gutteridge, T. R. R. Pettus, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 6563-6579; c) M. M. Victor, R. A. Pilli, Tetrahedron Lett. 1998, 39, 4421-4424.
108. For recent impressive demonstrations of the application of the Kishi-Nozaki coupling to natural products synthesis see: a) J. A. McCauley, K. Nagasawa, P. A. Lander, S. G. Mischke, M. A. Semones, Y. Kishi, J. Am. Chem. Soc. 1998, 120, 7647-7648; b) X.-T. Chen, S. K. Bhattacharya, B. Zhou, C. E. Gutteridge, T. R. R. Pettus, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 6563-6579; c) M. M. Victor, R. A. Pilli, Tetrahedron Lett. 1998, 39, 4421-4424.
109. A. L. Gemal, J.-L. Luche, J. Am. Chem. Soc. 1981, 103, 5454-5459.
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112. 13C NMR. The C15 spiroketal center of 1 resonates at about δ=95 (indicative of a [6,6]spiroketal ring), while the C15 center of 4 resonates at about δ=109 (indicative of a [5,6]spiroketal ring).
113. A second independent synthesis of reveromycin B (4) has been recently reported: T. Masuda, K. Osako, T. Shimizu, T. Nakata, Org. Lett. 1999, 1, 941-944.
114. Since the submission of this manuscript a third total synthesis of reveromycin B (4) has been reported: A. N. Cuzzupe, C. A. Hutton, M. J. Lilly, R. K. Mann, M. A. Rizzacasa, S. C. Zammit, Org. Lett. 2000, 2, 191-194.