Asymmetric synthesis of the polyol portion of the polyene macrolide antibiotic RK-397

Synlett

Volumn , Issue 12, 2002, Pages 2098-2100

  Schneider, Christoph ^a   Tolksdorf, Frank ^a   Rehfeuter, Markus ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Aldol reaction; Cope rearrangement; Polyene macrolide antibiotics; RK 397; Total synthesis

Indexed keywords

MACROLIDE; POLYENE ANTIBIOTIC AGENT; POLYOL; RK 397; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0036456193     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35584     Document Type: Article

References (32)

1. Kobinata, K.; Koshino, H.; Kudo, T.; Isono, K.; Osada, H. J. Antibiot. 1993, 46, 1616.
2. Koshino, H.; Kobinata, K.; Isono, K.; Osada, H. J. Antibiot. 1993, 46, 1619.
3. Suenaga, T.; Nakamura, H.; Koshino, H.; Kobinata, K.; Osada, H.; Nakata, T. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1997, 39, 607.
4. Omura, S. Macrolide Antibiotics: Chemistry, Biology, Practice; Academic Press: New York, 1984.
5. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
6. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
7. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
8. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
9. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
10. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
11. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
12. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
13. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
14. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
15. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
16. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
17. Reviews: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635. (b) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021. (c) Schneider, C. Angew. Chem. Int. Ed. 1998, 37, 1375; Angew. Chem. 1998, 110, 1445. (d) For selected examples see: Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360. (e) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753. (f) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299. (g) Weigand, S.; Brückner, R. Liebigs Ann. Recl. 1997, 1657. (h) Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. (i) Smith, A. B.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925. (j) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013. (k) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341. (l) Paterson, I.; Collet, L. A. Tetrahedron Lett. 2001, 42, 1187.
18. Review: Schneider, C. Synlett 2001, 1079; and references cited therein.
19. (a) Schneider, C.; Rehfeuter, M. Tetrahedron Lett. 1998, 39, 9.
20. (b) Schneider, C.; Rehfeuter, M. Chem.-Eur. J. 1999, 5, 2850.
21. Paterson, I.; Gibson, K. R.; Oballa, R. M. Tetrahedron Lett. 1996, 37, 8585.
22. Evans, D. A.; Coleman, P. J.; Cote, B. J. Org. Chem. 1997, 62, 788.
23. 11Si (829.15): C, 66.63; H, 8.75. Found: C, 66.82; H, 8.50.
24. Evans, D. A.; Duffy, J. L.; Dart, M. J. Tetrahedron Lett. 1994, 35, 8537.
25. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
26. 13C NMR see: Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
27. 14b with subsequent debenzylation and tetraacetonide formation the major stereoisomer contained two syn- and two anti-stereochemical relationships in agreement with the assigned configurations.
28. (b) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233.
29. (a) Wieland, H. Chem. Ber. 1912, 45, 484.
30. (b) Barbier, P.; Locquin, R. C. R. Chim. 1913, 156, 1443.
31. Burgess, E. M.; Penton, H. R.; Taylor, E. A. J. Org. Chem.; 1973, 38, 26.
32. 3] 715.4453. Found: 715.4531.