Design, synthesis, and biological properties of highly potent epothilone B analogues

Angewandte Chemie - International Edition

Volumn 42, Issue 30, 2003, Pages 3515-3520

  Nicolaou, K C ^a,b   Sasmal, Pradip K ^a,b   Rassias, Gerasimos ^a,b   Reddy, Mali Venkat ^a,b   Altmann, Karl Heinz ^c   Wartmann, Markus ^c   O'Brate, Aurora ^d   Giannakakou, Paraskevi ^d  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c NOVARTIS PHARMA AG   (Switzerland)

^d EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antitumor agents; Epothilones; Structure activity relationships; Sulfur; Total synthesis

Indexed keywords

SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TUMORS;

CANCER CELL LINES;

PROPANE;

CYCLOPROPANE; EPOTHILONE A; EPOTHILONE B; EPOTHILONE B DERIVATIVE; PACLITAXEL; PYRIDINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL DIVISION; CELL LINE, TUMOR; DRUG DESIGN; DRUG RESISTANCE; DRUG SCREENING ASSAYS, ANTITUMOR; EPOTHILONES; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; PACLITAXEL; STEREOISOMERISM;

EID: 0043032712     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351819     Document Type: Article

References (56)

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4. For selected reviews on the chemistry and biology of the epothilones, see: a) K.-H. Altmann, Mini-Rev. Med. Chem. 2003, 3, 149-158; b) R. Altaha, T. Fojo, E. Reed, J. Abraham, Curr. Pharm. Des. 2002, 8, 1707-1712; c) K. C. Nicolaou, A. Ritzén, K. Namato, Chem. Commun. 2001, 1523-1535; d) K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120-2153; Angew. Chem. Int. Ed. 1998, 37, 2014-2045.
5. For selected reviews on the chemistry and biology of the epothilones, see: a) K.-H. Altmann, Mini-Rev. Med. Chem. 2003, 3, 149-158; b) R. Altaha, T. Fojo, E. Reed, J. Abraham, Curr. Pharm. Des. 2002, 8, 1707-1712; c) K. C. Nicolaou, A. Ritzén, K. Namato, Chem. Commun. 2001, 1523-1535; d) K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120-2153; Angew. Chem. Int. Ed. 1998, 37, 2014-2045.
6. For selected reviews on the chemistry and biology of the epothilones, see: a) K.-H. Altmann, Mini-Rev. Med. Chem. 2003, 3, 149-158; b) R. Altaha, T. Fojo, E. Reed, J. Abraham, Curr. Pharm. Des. 2002, 8, 1707-1712; c) K. C. Nicolaou, A. Ritzén, K. Namato, Chem. Commun. 2001, 1523-1535; d) K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120-2153; Angew. Chem. Int. Ed. 1998, 37, 2014-2045.
7. For selected reviews on the chemistry and biology of the epothilones, see: a) K.-H. Altmann, Mini-Rev. Med. Chem. 2003, 3, 149-158; b) R. Altaha, T. Fojo, E. Reed, J. Abraham, Curr. Pharm. Des. 2002, 8, 1707-1712; c) K. C. Nicolaou, A. Ritzén, K. Namato, Chem. Commun. 2001, 1523-1535; d) K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120-2153; Angew. Chem. Int. Ed. 1998, 37, 2014-2045.
8. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
9. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
10. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
11. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
12. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
13. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
14. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
15. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
16. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
17. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
18. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
19. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
20. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
21. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
22. For recent total syntheses of epothilones and their analogues see: reviews (reference [2]) and a) A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899-2901; b) R. E. Taylor, Y. Chen, A. Beatty, J. Am. Chem. Soc. 2003, 125, 26-27; c) K.-H. Altmann, G. Bold, G. Caravatti, D. Denni, A. Flörsheimer, A. Schmidt, G. Rihs, M. Wartmann, Helv. Chim. Acta 2002, 85, 4086-4110; d) J. Sun, S. C. Sinha, Angew. Chem. 2002, 114, 1439-1441; Angew. Chem. Int. Ed. 2002, 41, 1381-1383; e) Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun, G. Li, Chem. Eur. J. 2002, 8, 3747-3756; f) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B.H. B. H. Long, G. D. Vite, Org. Lett. 2001, 3, 2693-2696; g) N. Martin, E. J. Thomas, Tetrahedron Lett. 2001, 42, 8373-8377; h) M. Valluri, R. M. Hindupur, B. Panicker, G. Labadie, J.-C. Jung, M. A. Avery, Org. Lett. 2001, 3, 3607-3609; i) C. B. Lee, Z. Wu, F. Zhang, M. D. Chappell, S. J. Stachel, T.-C. Chou, Y. Guan, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 5249-5259; j) H. J. Martin, P. Pojarliev, H. Kahlig, J. Mulzer, Chem. Eur. J. 2001, 7, 2261-2271; k) R. E. Taylor, Y. Chen, Org. Lett. 2001, 3, 2221-2224; l) J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407-5413; m) B. Zhu, J. S. Panek, Eur. J. Org. Chem. 2001, 9, 1701-1714; n) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
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47. 50 value for compound 7 was found to be 2.5 nM against the 1A9 cell line.
48. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, M. R. Boyd, J. Natl. Cancer Inst. 1990, 82, 1107-1112.
49. Note added in proof: After submission of this manuscript, a related article on epothilone analogues was published: F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622-2625; Angew. Chem. Int. Ed., 2003, 42, 2518-2521. See also: T. Carlomagno, M. J. J. Blommers, J. Meiler, W. Jahnke, T. Schupp, F. Petersen, D. Schinzer, K.-H. Altmann, C. Griesinger, Angew. Chem. 2003, 115, 2615-2619; Angew. Chem. Int. Ed., 2003, 42, 2511-2515; T. Carlomagno, V. M. Sanchez, M. J. J. Blommers, C. Griesinger, Angew. Chem. 2003, 115, 2619-2621; Angew. Chem. Int. Ed., 2003, 42, 2515-2517; R. I. Storer, T. Takemoto, P. S. Jackson, S. V. Ley, Angew. Chem. 2003, 115, 2625-2629; Angew. Chem. Int. Ed., 2003, 42, 2521-2525.
50. Note added in proof: After submission of this manuscript, a related article on epothilone analogues was published: F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622-2625; Angew. Chem. Int. Ed., 2003, 42, 2518-2521. See also: T. Carlomagno, M. J. J. Blommers, J. Meiler, W. Jahnke, T. Schupp, F. Petersen, D. Schinzer, K.-H. Altmann, C. Griesinger, Angew. Chem. 2003, 115, 2615-2619; Angew. Chem. Int. Ed., 2003, 42, 2511-2515; T. Carlomagno, V. M. Sanchez, M. J. J. Blommers, C. Griesinger, Angew. Chem. 2003, 115, 2619-2621; Angew. Chem. Int. Ed., 2003, 42, 2515-2517; R. I. Storer, T. Takemoto, P. S. Jackson, S. V. Ley, Angew. Chem. 2003, 115, 2625-2629; Angew. Chem. Int. Ed., 2003, 42, 2521-2525.
51. Note added in proof: After submission of this manuscript, a related article on epothilone analogues was published: F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622-2625; Angew. Chem. Int. Ed., 2003, 42, 2518-2521. See also: T. Carlomagno, M. J. J. Blommers, J. Meiler, W. Jahnke, T. Schupp, F. Petersen, D. Schinzer, K.-H. Altmann, C. Griesinger, Angew. Chem. 2003, 115, 2615-2619; Angew. Chem. Int. Ed., 2003, 42, 2511-2515; T. Carlomagno, V. M. Sanchez, M. J. J. Blommers, C. Griesinger, Angew. Chem. 2003, 115, 2619-2621; Angew. Chem. Int. Ed., 2003, 42, 2515-2517; R. I. Storer, T. Takemoto, P. S. Jackson, S. V. Ley, Angew. Chem. 2003, 115, 2625-2629; Angew. Chem. Int. Ed., 2003, 42, 2521-2525.
52. Note added in proof: After submission of this manuscript, a related article on epothilone analogues was published: F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622-2625; Angew. Chem. Int. Ed., 2003, 42, 2518-2521. See also: T. Carlomagno, M. J. J. Blommers, J. Meiler, W. Jahnke, T. Schupp, F. Petersen, D. Schinzer, K.-H. Altmann, C. Griesinger, Angew. Chem. 2003, 115, 2615-2619; Angew. Chem. Int. Ed., 2003, 42, 2511-2515; T. Carlomagno, V. M. Sanchez, M. J. J. Blommers, C. Griesinger, Angew. Chem. 2003, 115, 2619-2621; Angew. Chem. Int. Ed., 2003, 42, 2515-2517; R. I. Storer, T. Takemoto, P. S. Jackson, S. V. Ley, Angew. Chem. 2003, 115, 2625-2629; Angew. Chem. Int. Ed., 2003, 42, 2521-2525.
53. Note added in proof: After submission of this manuscript, a related article on epothilone analogues was published: F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622-2625; Angew. Chem. Int. Ed., 2003, 42, 2518-2521. See also: T. Carlomagno, M. J. J. Blommers, J. Meiler, W. Jahnke, T. Schupp, F. Petersen, D. Schinzer, K.-H. Altmann, C. Griesinger, Angew. Chem. 2003, 115, 2615-2619; Angew. Chem. Int. Ed., 2003, 42, 2511-2515; T. Carlomagno, V. M. Sanchez, M. J. J. Blommers, C. Griesinger, Angew. Chem. 2003, 115, 2619-2621; Angew. Chem. Int. Ed., 2003, 42, 2515-2517; R. I. Storer, T. Takemoto, P. S. Jackson, S. V. Ley, Angew. Chem. 2003, 115, 2625-2629; Angew. Chem. Int. Ed., 2003, 42, 2521-2525.
54. Note added in proof: After submission of this manuscript, a related article on epothilone analogues was published: F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622-2625; Angew. Chem. Int. Ed., 2003, 42, 2518-2521. See also: T. Carlomagno, M. J. J. Blommers, J. Meiler, W. Jahnke, T. Schupp, F. Petersen, D. Schinzer, K.-H. Altmann, C. Griesinger, Angew. Chem. 2003, 115, 2615-2619; Angew. Chem. Int. Ed., 2003, 42, 2511-2515; T. Carlomagno, V. M. Sanchez, M. J. J. Blommers, C. Griesinger, Angew. Chem. 2003, 115, 2619-2621; Angew. Chem. Int. Ed., 2003, 42, 2515-2517; R. I. Storer, T. Takemoto, P. S. Jackson, S. V. Ley, Angew. Chem. 2003, 115, 2625-2629; Angew. Chem. Int. Ed., 2003, 42, 2521-2525.
55. Note added in proof: After submission of this manuscript, a related article on epothilone analogues was published: F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622-2625; Angew. Chem. Int. Ed., 2003, 42, 2518-2521. See also: T. Carlomagno, M. J. J. Blommers, J. Meiler, W. Jahnke, T. Schupp, F. Petersen, D. Schinzer, K.-H. Altmann, C. Griesinger, Angew. Chem. 2003, 115, 2615-2619; Angew. Chem. Int. Ed., 2003, 42, 2511-2515; T. Carlomagno, V. M. Sanchez, M. J. J. Blommers, C. Griesinger, Angew. Chem. 2003, 115, 2619-2621; Angew. Chem. Int. Ed., 2003, 42, 2515-2517; R. I. Storer, T. Takemoto, P. S. Jackson, S. V. Ley, Angew. Chem. 2003, 115, 2625-2629; Angew. Chem. Int. Ed., 2003, 42, 2521-2525.
56. Note added in proof: After submission of this manuscript, a related article on epothilone analogues was published: F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622-2625; Angew. Chem. Int. Ed., 2003, 42, 2518-2521. See also: T. Carlomagno, M. J. J. Blommers, J. Meiler, W. Jahnke, T. Schupp, F. Petersen, D. Schinzer, K.-H. Altmann, C. Griesinger, Angew. Chem. 2003, 115, 2615-2619; Angew. Chem. Int. Ed., 2003, 42, 2511-2515; T. Carlomagno, V. M. Sanchez, M. J. J. Blommers, C. Griesinger, Angew. Chem. 2003, 115, 2619-2621; Angew. Chem. Int. Ed., 2003, 42, 2515-2517; R. I. Storer, T. Takemoto, P. S. Jackson, S. V. Ley, Angew. Chem. 2003, 115, 2625-2629; Angew. Chem. Int. Ed., 2003, 42, 2521-2525.