A general and stereocontrolled strategy for the iterative assembly of enantiopure polypropionate subunits: Synthesis of the C19-C28 segment of rifamycin S from a single chiron

Journal of the American Chemical Society

Volumn 119, Issue 42, 1997, Pages 10034-10041

  Hanessian, Stephen ^a   Wang, Wengui ^a   Gai, Yonghua ^a   Olivier, Eric ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

RIFAMYCIN S;

ARTICLE; DIASTEREOISOMER; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030724134     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970251g     Document Type: Article

References (72)

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34. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
35. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
36. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
37. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
38. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
39. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
40. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
41. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
42. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
43. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
44. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
45. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
46. For the synthesis of the ansa chain, see: (c) Nakata, M.; Takao, H.; Ikeyyama, Y.; Sakai, T.; Tatsuta, K.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1981, 54, 1749. (d) Masamune, S.; Imperiali, B.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5528. (e) Hanessian, S.; Pougny, J. -R.; Bossenkool, I. K. J. Am. Chem. Soc. 1982, 104, 6164. (f) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487. (g) Fraser-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731. (h) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862. (i) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (j) Ziegler, F. E.; Cain W. T.; Kneisley, A.; Stirchak, E. P.; Wester, R. T. J. Am. Chem. Soc. 1988, 110, 5442. (k) Katsuki, T.; Hanamota, T.; Yamaguchi, M. Chem. Lett. 1989, 117. (I) Paterson, I.; McClure C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293. (m) Harada, T.; Kagamihara, Y.; Tanaka, S.; Sakamoto, K.; Oku, A. J. Org. Chem. 1992, 57, 1637. (n) Lautens, M.; Belter, R. K. Tetrahedron Lett. 1992, 33, 2617. (o) Miyashita, M.; Yoshihara, K.; Kawamine, K.; Hoshino, M.; Irie, H. Tetrahedron Lett. 1993, 34, 6285.
47. For a computer-aided prediction of stereochemical array in macrolides and ionophores, see: Hanessian, S.; Botta, M.; Larouche, B.; Boyaroglu, A. J. Chem. Inf. Comput. Sci. 1992, 32, 718.
48. Isolation and structure elucidation, see: (a) Arai, M. J. Antibiot. Ser. A 1960, 13, 46, 51. (b) Takahashi, S.; Ohki, E. Chem. Pharm. Bull. 1967, 15, 1726. (c) Kaiser, H.; Keller-Seheirlein, W. Helv. Chim. Acta 1981, 64, 407. (d) Neupert-Laves, K.; Dobler, M. Helv. Chim. Acta 1982, 65, 262.
49. Isolation and structure elucidation, see: (a) Arai, M. J. Antibiot. Ser. A 1960, 13, 46, 51. (b) Takahashi, S.; Ohki, E. Chem. Pharm. Bull. 1967, 15, 1726. (c) Kaiser, H.; Keller-Seheirlein, W. Helv. Chim. Acta 1981, 64, 407. (d) Neupert-Laves, K.; Dobler, M. Helv. Chim. Acta 1982, 65, 262.
50. Isolation and structure elucidation, see: (a) Arai, M. J. Antibiot. Ser. A 1960, 13, 46, 51. (b) Takahashi, S.; Ohki, E. Chem. Pharm. Bull. 1967, 15, 1726. (c) Kaiser, H.; Keller-Seheirlein, W. Helv. Chim. Acta 1981, 64, 407. (d) Neupert-Laves, K.; Dobler, M. Helv. Chim. Acta 1982, 65, 262.
51. Isolation and structure elucidation, see: (a) Arai, M. J. Antibiot. Ser. A 1960, 13, 46, 51. (b) Takahashi, S.; Ohki, E. Chem. Pharm. Bull. 1967, 15, 1726. (c) Kaiser, H.; Keller-Seheirlein, W. Helv. Chim. Acta 1981, 64, 407. (d) Neupert-Laves, K.; Dobler, M. Helv. Chim. Acta 1982, 65, 262.
52. Isolation and structure elucidation, see: (a)Werner, G.; Hagenmaier, H.; Albert, K.; Kohlshorn, H.; Drautz, H. Tetrahedron Lett. 1983, 24, 5193. (b) Corey, E. J.; Ponder, J. W. Tetrahedron Lett. 1984, 25, 4325. (c) Baker, G. H.; Brown, P. J.; Dorgan, R. J. J.; Everett, J. R.; Ley, S. V.; Slawin, A. M. Z; Williams, D. J. Tetrahedron Lett. 1987, 28, 5565.
53. Isolation and structure elucidation, see: (a)Werner, G.; Hagenmaier, H.; Albert, K.; Kohlshorn, H.; Drautz, H. Tetrahedron Lett. 1983, 24, 5193. (b) Corey, E. J.; Ponder, J. W. Tetrahedron Lett. 1984, 25, 4325. (c) Baker, G. H.; Brown, P. J.; Dorgan, R. J. J.; Everett, J. R.; Ley, S. V.; Slawin, A. M. Z; Williams, D. J. Tetrahedron Lett. 1987, 28, 5565.
54. Isolation and structure elucidation, see: (a)Werner, G.; Hagenmaier, H.; Albert, K.; Kohlshorn, H.; Drautz, H. Tetrahedron Lett. 1983, 24, 5193. (b) Corey, E. J.; Ponder, J. W. Tetrahedron Lett. 1984, 25, 4325. (c) Baker, G. H.; Brown, P. J.; Dorgan, R. J. J.; Everett, J. R.; Ley, S. V.; Slawin, A. M. Z; Williams, D. J. Tetrahedron Lett. 1987, 28, 5565.
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60. For the total synthesis, see: (a) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (b) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Murase, H.; Yoshida, T.; Matsumura, S.; Nakata, M. Tetrahedron Lett. 1996, 37, 1069. (c) Toshima, K.; Yamaguchi, H.; Jyojima, T.; Noguchi, Y.; Nakata, M.; Matsumura, S. Tetrahedron Lett. 1996, 37, 1073. (d) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Noguchi, Y.; Yoshida, T.; Murase, H.; Nakata, M.; Matsumura, S. J. Org. Chem. 1997, 62, 3271.
61. For the total synthesis, see: (a) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (b) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Murase, H.; Yoshida, T.; Matsumura, S.; Nakata, M. Tetrahedron Lett. 1996, 37, 1069. (c) Toshima, K.; Yamaguchi, H.; Jyojima, T.; Noguchi, Y.; Nakata, M.; Matsumura, S. Tetrahedron Lett. 1996, 37, 1073. (d) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Noguchi, Y.; Yoshida, T.; Murase, H.; Nakata, M.; Matsumura, S. J. Org. Chem. 1997, 62, 3271.
62. For the total synthesis, see: (a) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (b) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Murase, H.; Yoshida, T.; Matsumura, S.; Nakata, M. Tetrahedron Lett. 1996, 37, 1069. (c) Toshima, K.; Yamaguchi, H.; Jyojima, T.; Noguchi, Y.; Nakata, M.; Matsumura, S. Tetrahedron Lett. 1996, 37, 1073. (d) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Noguchi, Y.; Yoshida, T.; Murase, H.; Nakata, M.; Matsumura, S. J. Org. Chem. 1997, 62, 3271.
63. For the total synthesis, see: (a) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (b) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Murase, H.; Yoshida, T.; Matsumura, S.; Nakata, M. Tetrahedron Lett. 1996, 37, 1069. (c) Toshima, K.; Yamaguchi, H.; Jyojima, T.; Noguchi, Y.; Nakata, M.; Matsumura, S. Tetrahedron Lett. 1996, 37, 1073. (d) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Noguchi, Y.; Yoshida, T.; Murase, H.; Nakata, M.; Matsumura, S. J. Org. Chem. 1997, 62, 3271.
64. For the synthesis of segments, see: (e) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587. (f) Roush, W. R.; Bannister, T. D.; Wendt, M. D. Tetrahedron Lett. 1993, 34, 8387. (g) Paterson, I.; Bower, S.; Mcleod. M. D. Tetrahedron Lett. 1995, 36, 175.
65. For the synthesis of segments, see: (e) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587. (f) Roush, W. R.; Bannister, T. D.; Wendt, M. D. Tetrahedron Lett. 1993, 34, 8387. (g) Paterson, I.; Bower, S.; Mcleod. M. D. Tetrahedron Lett. 1995, 36, 175.
66. For the synthesis of segments, see: (e) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587. (f) Roush, W. R.; Bannister, T. D.; Wendt, M. D. Tetrahedron Lett. 1993, 34, 8387. (g) Paterson, I.; Bower, S.; Mcleod. M. D. Tetrahedron Lett. 1995, 36, 175.
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