Total syntheses of depsipeptide elastase inhibitors YM-47141 and YM- 47142 with use of ylide protection and coupling methods [12]

Journal of the American Chemical Society

Volumn 121, Issue 6, 1999, Pages 1401-1402

  Wasserman, Harry H ^a   Chen, Jyun Hung ^a   Xia, Mingde ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; DEPSIPEPTIDE; ELASTASE INHIBITOR; MACROLIDE; NATURAL PRODUCT; RAPAMYCIN; TACROLIMUS; TRICARBOXYLIC ACID; UNCLASSIFIED DRUG; YM 47141; YM 47142;

ANTIMICROBIAL ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; LETTER; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0033576984     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9840302     Document Type: Letter

References (34)

1. Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Goto, T.; Hahimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 109, 5031.
2. (a) FK-506: Kino, T.; Hatanaka, H.; Hashimoto, M.; Nishyama, M.; Goto, T.; Okuhara, M.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1987, 40, 1249.
3. (b) FR-900525: Hatanaka, H.; Kino, T.; Asano, M.; Goto, T.; Tanaka, H.; Okuhara, M. J. Antibiot. 1989, 42, 620.
4. (c) FR-900520 and FR-900523: Hatanaka, H.; Kino, T.; Miyata, S.; Inamura, N.; Kuroda, A.; Goto, T.; Tanaka, H.; Okuhara, M. J. Antibiot. 1988, 41, 1592.
5. (d) Rapamycin: Swindelly, D.; White, P.; Findlay, J. Can. J. Chem. 1978, 56, 2491. Martel, R.; Klicius, J.; Galet, S. Can. J. Physiol. Pharmacol. 1977, 55, 48.
6. (d) Rapamycin: Swindelly, D.; White, P.; Findlay, J. Can. J. Chem. 1978, 56, 2491. Martel, R.; Klicius, J.; Galet, S. Can. J. Physiol. Pharmacol. 1977, 55, 48.
7. (a) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998.
8. (b) Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419.
9. (c) Romo, D.; Meyer, S. D.; Johnson, D. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 7906.
10. Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345.
11. (e) (i) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1995, 117, 5407-5408. (ii) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961 and 962-973.
12. (e) (i) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1995, 117, 5407-5408. (ii) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947-961 and 962-973.
13. (f) For a recent total synthesis of FK-506 and other references to synthetic work in this field, see: Ireland, R. E.; Liu, L.; Roper, T. D. Tetrahedron 1997, 53, 13221 Ireland, R. E.; Liu, L.; Roper, T. D.; Gleason, J. L. Tetrahedron 1997, 53, 13257.
14. (f) For a recent total synthesis of FK-506 and other references to synthetic work in this field, see: Ireland, R. E.; Liu, L.; Roper, T. D. Tetrahedron 1997, 53, 13221 Ireland, R. E.; Liu, L.; Roper, T. D.; Gleason, J. L. Tetrahedron 1997, 53, 13257.
15. (a) Egbertson, M.; Danishefsky S. J. J. Org. Chem. 1989, 54, 11.
16. (b) Villalobos, A.; Danishefsky S. J. J. Org. Chem. 1989, 54, 12.
17. (c) Schreiber, S. L.; Sammakia, T.; Uehling, D. E. J. Org. Chem. 1989, 54, 15.
18. (d) Jones, A. B.; Yamaguchi, M.; Patten, A.; Danishefsky, S. J.; Ragan, J. A.; Smith, D. B.; Schreiber, S. L. J. Org. Chem. 1989, 54, 17.
19. (e) Schreiber, S. L.; Smith, D. B. J. Org. Chem. 1989, 54, 9.
20. (f) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167.
21. (g) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 54, 2785.
22. (h) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
23. (a) Yasumuro, K.; Suzuki, Y.; Shibaraki, M.; Teramura, K.; Abe, K.; Orita, M. J. Antibiot. 1995, 48, 1425.
24. (b) Orita, M.; Yasumuro, K.; Kokubo, K.; Shimizu, M.; Abe, K.; Tokunaza, T.; Kaniwa, H. J. Antibiot. 1995, 48, 1430.
25. Wasserman, H. H.; Ho, W.-B. J. Org. Chem. 1994, 59, 4364.
26. Wasserman, H. H.; Petersen, A. K. Tetrahedron Lett. 1997, 38, 953.
27. Wasserman, H. H.; Petersen, A. K. J. Org. Chem. 1997, 62, 8972.
28. (a) Luengo, J. I.; Rozamus, L. W.; Holt, D. A. Tetrahedron Lett. 1993, 34, 4599.
29. (b) Fisher, M. J.; Chow, K.; Villalobos, A.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2900.
30. Luengo, J. I.; Konialian, A. L.; Holt, D. A. Tetrahedron Lett. 1993, 34, 991.
31. (a) König, W.; Geiger, R. Chem. Ber. 1970, 103, 2041.
32. (b) Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251.
33. We were mindful of possible side reactions in this last step: sensitivity of the primary amide group and secondary alcohol group toward oxidation, β-elimination of the free threonine hydroxyl in the conversion of 9 to 1. These concerns were allayed by model studies of primary amide units and threonine residues in small peptides, which were stable to the conditions of low-temperature ozonolysis.
34. 1H NMR peaks corresponding to the methine and methylene protons at the γ and δ positions of Dah were indistinguishable from the corresponding absorptions in the natural products. There were no additional peaks in the synthetic product to indicate any epimerization.