Intramolecular aminolysis of trichloroethyl esters: A mild macrocyclization protocol for the preparation of cryptophycin derivatives

Tetrahedron Asymmetry

Volumn 9, Issue 16, 1998, Pages 2777-2781

  Fray, Andrew H ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYPTOPHYCIN DERIVATIVE; ESTER; MACROLIDE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW;

EID: 0032555559     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00287-0     Document Type: Article

References (27)

1. Golakoti, T.; Ogino, J.; Heltzel, C. E.; Husrebo, T. L.; Jensen, C. M.; Larsen, L. K.; Patterson, G. M. L.; Moore, R. E.; Moobery, S. L.; Corbett, T. H.; Valeriote, F. A. J. Am. Chem. Soc. 1995, 117, 12030-12049.
2. (a) Barrow, R. A.; Hemscheidt, T.; Liang, J.; Paik, S.; Moore, R. E.; Tius, M. A. J. Am. Chem. Soc. 1995, 117, 2479-2490;
3. (b) Moore, R. E.; Tius, M. A.; Barrow, R. A.; Liang, J.; Corbett, T. H.; Valeriote, F. A.; Hemscheidt, T. K., US Pat. Appl. US 95-400057.
4. Salamonczyk, G. M.; Han, K.; Guo, Z.-W.; Sih, C. J. J. Org. Chem. 1996, 61, 6893-6900; DeMuys, J.-M.; Rej, R.; Nguyen, D.; Go, B.; Fortin, S.; Lavellee, J.-F. Bioorg. Med. Chem. Lett. 1996, 6, 1111-1116; Rej, R.; Nguyen, D.; Go, B.; Fortin, S.; Lavellee, J.-F. J. Org. Chem. 1996, 61(18), 6289-6285.
5. Salamonczyk, G. M.; Han, K.; Guo, Z.-W.; Sih, C. J. J. Org. Chem. 1996, 61, 6893-6900; DeMuys, J.-M.; Rej, R.; Nguyen, D.; Go, B.; Fortin, S.; Lavellee, J.-F. Bioorg. Med. Chem. Lett. 1996, 6, 1111-1116; Rej, R.; Nguyen, D.; Go, B.; Fortin, S.; Lavellee, J.-F. J. Org. Chem. 1996, 61(18), 6289-6285.
6. Salamonczyk, G. M.; Han, K.; Guo, Z.-W.; Sih, C. J. J. Org. Chem. 1996, 61, 6893-6900; DeMuys, J.-M.; Rej, R.; Nguyen, D.; Go, B.; Fortin, S.; Lavellee, J.-F. Bioorg. Med. Chem. Lett. 1996, 6, 1111-1116; Rej, R.; Nguyen, D.; Go, B.; Fortin, S.; Lavellee, J.-F. J. Org. Chem. 1996, 61(18), 6289-6285.
7. Kobayashi, M.; Wang, W.; Ohyabu, N.; Kurosu, M.; Kitagawa, I. Chem. Pharm. Bull. 1995, 43(9), 1598-1600.
8. Exceptions are cyclization by ester bond formation: Gardinier, K. M.; Leahy, J. W. J. Org. Chem. 1997, 62(21), 7098-7099, and by olefin bond formation: Kobayashi, M.; Kurosu, M.; Wang, W.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 2394-2396.
9. Exceptions are cyclization by ester bond formation: Gardinier, K. M.; Leahy, J. W. J. Org. Chem. 1997, 62(21), 7098-7099, and by olefin bond formation: Kobayashi, M.; Kurosu, M.; Wang, W.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 2394-2396.
10. Intramolecular aminolyses: (a) Gisin, B. F.; Merrifield, R. B. J. Am. Chem. Soc. 1972, 94, 3102; (b) Kirk, K. L.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 8142; (c) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1976, 98, 6978; (d) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1979, 101, 7379 and references therein; (e) Wasserman, H. H.; Robinson, R. P.; Carter, C. G. J. Am. Chem. Soc. 1983, 105(6), 1697-1698; Mutoh, R.; Shirai, R.; Koiso, Y.; Iwasaki, S. Heterocycles 1995, 41(1), 9-12; Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569-1570.
11. Intramolecular aminolyses: (a) Gisin, B. F.; Merrifield, R. B. J. Am. Chem. Soc. 1972, 94, 3102; (b) Kirk, K. L.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 8142; (c) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1976, 98, 6978; (d) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1979, 101, 7379 and references therein; (e) Wasserman, H. H.; Robinson, R. P.; Carter, C. G. J. Am. Chem. Soc. 1983, 105(6), 1697-1698; Mutoh, R.; Shirai, R.; Koiso, Y.; Iwasaki, S. Heterocycles 1995, 41(1), 9-12; Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569-1570.
12. Intramolecular aminolyses: (a) Gisin, B. F.; Merrifield, R. B. J. Am. Chem. Soc. 1972, 94, 3102; (b) Kirk, K. L.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 8142; (c) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1976, 98, 6978; (d) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1979, 101, 7379 and references therein; (e) Wasserman, H. H.; Robinson, R. P.; Carter, C. G. J. Am. Chem. Soc. 1983, 105(6), 1697-1698; Mutoh, R.; Shirai, R.; Koiso, Y.; Iwasaki, S. Heterocycles 1995, 41(1), 9-12; Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569-1570.
13. Intramolecular aminolyses: (a) Gisin, B. F.; Merrifield, R. B. J. Am. Chem. Soc. 1972, 94, 3102; (b) Kirk, K. L.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 8142; (c) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1976, 98, 6978; (d) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1979, 101, 7379 and references therein; (e) Wasserman, H. H.; Robinson, R. P.; Carter, C. G. J. Am. Chem. Soc. 1983, 105(6), 1697-1698; Mutoh, R.; Shirai, R.; Koiso, Y.; Iwasaki, S. Heterocycles 1995, 41(1), 9-12; Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569-1570.
14. Intramolecular aminolyses: (a) Gisin, B. F.; Merrifield, R. B. J. Am. Chem. Soc. 1972, 94, 3102; (b) Kirk, K. L.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 8142; (c) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1976, 98, 6978; (d) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1979, 101, 7379 and references therein; (e) Wasserman, H. H.; Robinson, R. P.; Carter, C. G. J. Am. Chem. Soc. 1983, 105(6), 1697-1698; Mutoh, R.; Shirai, R.; Koiso, Y.; Iwasaki, S. Heterocycles 1995, 41(1), 9-12; Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569-1570.
15. Intramolecular aminolyses: (a) Gisin, B. F.; Merrifield, R. B. J. Am. Chem. Soc. 1972, 94, 3102; (b) Kirk, K. L.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 8142; (c) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1976, 98, 6978; (d) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1979, 101, 7379 and references therein; (e) Wasserman, H. H.; Robinson, R. P.; Carter, C. G. J. Am. Chem. Soc. 1983, 105(6), 1697-1698; Mutoh, R.; Shirai, R.; Koiso, Y.; Iwasaki, S. Heterocycles 1995, 41(1), 9-12; Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569-1570.
16. Intramolecular aminolyses: (a) Gisin, B. F.; Merrifield, R. B. J. Am. Chem. Soc. 1972, 94, 3102; (b) Kirk, K. L.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 8142; (c) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1976, 98, 6978; (d) Fife, T. H.; DeMark, B. R. J. Am. Chem. Soc. 1979, 101, 7379 and references therein; (e) Wasserman, H. H.; Robinson, R. P.; Carter, C. G. J. Am. Chem. Soc. 1983, 105(6), 1697-1698; Mutoh, R.; Shirai, R.; Koiso, Y.; Iwasaki, S. Heterocycles 1995, 41(1), 9-12; Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569-1570.
17. Bimolecular aminolyses: (a) amides: Su, C.-W.; Watson, J. J. Am. Chem. Soc. 1974, 96(6), 1854-1857; (b) carboxylate: Menger, F. M.; Vitale, A. C. J. Am. Chem. Soc. 1973, 95(15), 4931-4934; (c) 2-hydroxypyridine: Rony, P. R. J. Am. Chem. Soc. 1969, 91(22), 6090-6096; (d) Nakamizo, N. Bull. Chem. Soc. Jpn 1969, 42(4), 1071-1077; (e) Robins, M. J.; Sarker, S.; Xie, M.; Zhang, W.; Peterson, M. A. Tetrahedron Lett. 1996, 37(23), 3921-3924; (f) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. C. 1969, 1, 89-91; (g) nucleosides: Melander, C.; Home, D. A. J. Org. Chem. 1997, 62(26), 9295-9297; (h) DMAP: Cossy, J.; Thellend, A. Synthesis 1989, 753-755.
18. Bimolecular aminolyses: (a) amides: Su, C.-W.; Watson, J. J. Am. Chem. Soc. 1974, 96(6), 1854-1857; (b) carboxylate: Menger, F. M.; Vitale, A. C. J. Am. Chem. Soc. 1973, 95(15), 4931-4934; (c) 2-hydroxypyridine: Rony, P. R. J. Am. Chem. Soc. 1969, 91(22), 6090-6096; (d) Nakamizo, N. Bull. Chem. Soc. Jpn 1969, 42(4), 1071-1077; (e) Robins, M. J.; Sarker, S.; Xie, M.; Zhang, W.; Peterson, M. A. Tetrahedron Lett. 1996, 37(23), 3921-3924; (f) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. C. 1969, 1, 89-91; (g) nucleosides: Melander, C.; Home, D. A. J. Org. Chem. 1997, 62(26), 9295-9297; (h) DMAP: Cossy, J.; Thellend, A. Synthesis 1989, 753-755.
19. Bimolecular aminolyses: (a) amides: Su, C.-W.; Watson, J. J. Am. Chem. Soc. 1974, 96(6), 1854-1857; (b) carboxylate: Menger, F. M.; Vitale, A. C. J. Am. Chem. Soc. 1973, 95(15), 4931-4934; (c) 2-hydroxypyridine: Rony, P. R. J. Am. Chem. Soc. 1969, 91(22), 6090-6096; (d) Nakamizo, N. Bull. Chem. Soc. Jpn 1969, 42(4), 1071-1077; (e) Robins, M. J.; Sarker, S.; Xie, M.; Zhang, W.; Peterson, M. A. Tetrahedron Lett. 1996, 37(23), 3921-3924; (f) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. C. 1969, 1, 89-91; (g) nucleosides: Melander, C.; Home, D. A. J. Org. Chem. 1997, 62(26), 9295-9297; (h) DMAP: Cossy, J.; Thellend, A. Synthesis 1989, 753-755.
20. Bimolecular aminolyses: (a) amides: Su, C.-W.; Watson, J. J. Am. Chem. Soc. 1974, 96(6), 1854-1857; (b) carboxylate: Menger, F. M.; Vitale, A. C. J. Am. Chem. Soc. 1973, 95(15), 4931-4934; (c) 2-hydroxypyridine: Rony, P. R. J. Am. Chem. Soc. 1969, 91(22), 6090-6096; (d) Nakamizo, N. Bull. Chem. Soc. Jpn 1969, 42(4), 1071-1077; (e) Robins, M. J.; Sarker, S.; Xie, M.; Zhang, W.; Peterson, M. A. Tetrahedron Lett. 1996, 37(23), 3921-3924; (f) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. C. 1969, 1, 89-91; (g) nucleosides: Melander, C.; Home, D. A. J. Org. Chem. 1997, 62(26), 9295-9297; (h) DMAP: Cossy, J.; Thellend, A. Synthesis 1989, 753-755.
21. Bimolecular aminolyses: (a) amides: Su, C.-W.; Watson, J. J. Am. Chem. Soc. 1974, 96(6), 1854-1857; (b) carboxylate: Menger, F. M.; Vitale, A. C. J. Am. Chem. Soc. 1973, 95(15), 4931-4934; (c) 2-hydroxypyridine: Rony, P. R. J. Am. Chem. Soc. 1969, 91(22), 6090-6096; (d) Nakamizo, N. Bull. Chem. Soc. Jpn 1969, 42(4), 1071-1077; (e) Robins, M. J.; Sarker, S.; Xie, M.; Zhang, W.; Peterson, M. A. Tetrahedron Lett. 1996, 37(23), 3921-3924; (f) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. C. 1969, 1, 89-91; (g) nucleosides: Melander, C.; Home, D. A. J. Org. Chem. 1997, 62(26), 9295-9297; (h) DMAP: Cossy, J.; Thellend, A. Synthesis 1989, 753-755.
22. Bimolecular aminolyses: (a) amides: Su, C.-W.; Watson, J. J. Am. Chem. Soc. 1974, 96(6), 1854-1857; (b) carboxylate: Menger, F. M.; Vitale, A. C. J. Am. Chem. Soc. 1973, 95(15), 4931-4934; (c) 2-hydroxypyridine: Rony, P. R. J. Am. Chem. Soc. 1969, 91(22), 6090-6096; (d) Nakamizo, N. Bull. Chem. Soc. Jpn 1969, 42(4), 1071-1077; (e) Robins, M. J.; Sarker, S.; Xie, M.; Zhang, W.; Peterson, M. A. Tetrahedron Lett. 1996, 37(23), 3921-3924; (f) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. C. 1969, 1, 89-91; (g) nucleosides: Melander, C.; Home, D. A. J. Org. Chem. 1997, 62(26), 9295-9297; (h) DMAP: Cossy, J.; Thellend, A. Synthesis 1989, 753-755.
23. Bimolecular aminolyses: (a) amides: Su, C.-W.; Watson, J. J. Am. Chem. Soc. 1974, 96(6), 1854-1857; (b) carboxylate: Menger, F. M.; Vitale, A. C. J. Am. Chem. Soc. 1973, 95(15), 4931-4934; (c) 2-hydroxypyridine: Rony, P. R. J. Am. Chem. Soc. 1969, 91(22), 6090-6096; (d) Nakamizo, N. Bull. Chem. Soc. Jpn 1969, 42(4), 1071-1077; (e) Robins, M. J.; Sarker, S.; Xie, M.; Zhang, W.; Peterson, M. A. Tetrahedron Lett. 1996, 37(23), 3921-3924; (f) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. C. 1969, 1, 89-91; (g) nucleosides: Melander, C.; Home, D. A. J. Org. Chem. 1997, 62(26), 9295-9297; (h) DMAP: Cossy, J.; Thellend, A. Synthesis 1989, 753-755.
24. Bimolecular aminolyses: (a) amides: Su, C.-W.; Watson, J. J. Am. Chem. Soc. 1974, 96(6), 1854-1857; (b) carboxylate: Menger, F. M.; Vitale, A. C. J. Am. Chem. Soc. 1973, 95(15), 4931-4934; (c) 2-hydroxypyridine: Rony, P. R. J. Am. Chem. Soc. 1969, 91(22), 6090-6096; (d) Nakamizo, N. Bull. Chem. Soc. Jpn 1969, 42(4), 1071-1077; (e) Robins, M. J.; Sarker, S.; Xie, M.; Zhang, W.; Peterson, M. A. Tetrahedron Lett. 1996, 37(23), 3921-3924; (f) Openshaw, H. T.; Whittaker, N. J. Chem. Soc. C. 1969, 1, 89-91; (g) nucleosides: Melander, C.; Home, D. A. J. Org. Chem. 1997, 62(26), 9295-9297; (h) DMAP: Cossy, J.; Thellend, A. Synthesis 1989, 753-755.
25. (a) Menger, F. M.; Smith, J. H. Tetrahedron Lett. 1970, 48, 4163;
26. (b) Menger, F. M.; Smith, J. H. J. Am. Chem. Soc. 1972, 94(11), 3824-3829.
27. The use of excess 2-hydroxypyridine was found to give complete reactions within 14-16 h (overnight).