Application of glycosyltetrazoles in oligosaccharide synthesis: Assembly of the C3 trisaccharide component of the antibiotic PI-080

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 6-7

  Sobti, Aditya ^a   Kim, Kyungjin ^a   Sulikowski, Gary A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; ANTIBIOTIC PI 080; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030030626     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951954o     Document Type: Article

References (37)

1. For an excellent review of angucycline antibiotics, see: Rohr, J.; Thiericke, R. Nat. Prod. Rep. 1992, 9, 103-137.
2. PI-080: (a) Kawashima, A.; Kishimura, Y.; Tamai, M.; Kanada, K. Chem. Pharm. Bull. 1989, 37, 3429-3431.
3. PI-6621: (b) Kawashima, A.; Yoshimura, Y.; Kamigori, K.; Yagishi, M.; Mizutani, T. Chem. Abstr. 1989, 114, 22464d.
4. For recent examples of a glycosylation of a tertiary alcohol, see: (a) Corey, E. J.; Wu, Y.-J. J. Am. Chem. Soc. 1993, 115, 8871-8872. (b) Hatakeyama, S.; Kawamura, M.; Takano, S. J. Am. Chem. Soc. 1994, 116 4081-4082. (c) Yan, L.; Kahne, D. Synlett 1995, 523-524.
5. For recent examples of a glycosylation of a tertiary alcohol, see: (a) Corey, E. J.; Wu, Y.-J. J. Am. Chem. Soc. 1993, 115, 8871-8872. (b) Hatakeyama, S.; Kawamura, M.; Takano, S. J. Am. Chem. Soc. 1994, 116 4081-4082. (c) Yan, L.; Kahne, D. Synlett 1995, 523-524.
6. For recent examples of a glycosylation of a tertiary alcohol, see: (a) Corey, E. J.; Wu, Y.-J. J. Am. Chem. Soc. 1993, 115, 8871-8872. (b) Hatakeyama, S.; Kawamura, M.; Takano, S. J. Am. Chem. Soc. 1994, 116 4081-4082. (c) Yan, L.; Kahne, D. Synlett 1995, 523-524.
7. Anthracycline antibiotics: (a) Thiem, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D., Hawkins, L. D., McGarvey, G. J., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; Chapter 8. (b) Monneret, C.; Martin, A.; Pais, M. J. Carbohydr. Chem. 1988, 7, 417-434. (c) Suzuki, K; Sulikowski, G. A.; Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 8895-8902. (d) Kolar, C.; Kneissl, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 809-811. (e) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581.
8. Anthracycline antibiotics: (a) Thiem, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D., Hawkins, L. D., McGarvey, G. J., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; Chapter 8. (b) Monneret, C.; Martin, A.; Pais, M. J. Carbohydr. Chem. 1988, 7, 417-434. (c) Suzuki, K; Sulikowski, G. A.; Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 8895-8902. (d) Kolar, C.; Kneissl, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 809-811. (e) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581.
9. Anthracycline antibiotics: (a) Thiem, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D., Hawkins, L. D., McGarvey, G. J., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; Chapter 8. (b) Monneret, C.; Martin, A.; Pais, M. J. Carbohydr. Chem. 1988, 7, 417-434. (c) Suzuki, K; Sulikowski, G. A.; Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 8895-8902. (d) Kolar, C.; Kneissl, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 809-811. (e) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581.
10. Anthracycline antibiotics: (a) Thiem, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D., Hawkins, L. D., McGarvey, G. J., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; Chapter 8. (b) Monneret, C.; Martin, A.; Pais, M. J. Carbohydr. Chem. 1988, 7, 417-434. (c) Suzuki, K; Sulikowski, G. A.; Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 8895-8902. (d) Kolar, C.; Kneissl, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 809-811. (e) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581.
11. Anthracycline antibiotics: (a) Thiem, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D., Hawkins, L. D., McGarvey, G. J., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; Chapter 8. (b) Monneret, C.; Martin, A.; Pais, M. J. Carbohydr. Chem. 1988, 7, 417-434. (c) Suzuki, K; Sulikowski, G. A.; Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 8895-8902. (d) Kolar, C.; Kneissl, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 809-811. (e) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581.
12. Aureolic acid antibiotics: (f) Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954-958. (g) Thiem, J.; Gerkeno, M.; Schottmer, B.; Weigand, J. Carbohydr Res. 1987, 164, 327-341. (h) Thiem, J.; Meyer, B. Tetrahedron 1981, 37, 551-558. (i) Roush, W. R.; Lin, X.-F. J. Am Chem. Soc. 1995, 117, 2236-2250 and references cited within. (j) Toshima, K.; Nozaki, Y ; Mukaiyama, S.; Tamai, T.; Nakata, M.; Tatsuta, K.; Kinoshita, M. J. Am. Chem. Soc. 1995, 117, 3717-3727 and references cited within. (k) Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960-962. (l) Crich, D.; Ritchie, T. J. J. Chem. Soc., Chem. Commun. 1988, 1461-1463.
13. Aureolic acid antibiotics: (f) Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954-958. (g) Thiem, J.; Gerkeno, M.; Schottmer, B.; Weigand, J. Carbohydr Res. 1987, 164, 327-341. (h) Thiem, J.; Meyer, B. Tetrahedron 1981, 37, 551-558. (i) Roush, W. R.; Lin, X.-F. J. Am Chem. Soc. 1995, 117, 2236-2250 and references cited within. (j) Toshima, K.; Nozaki, Y ; Mukaiyama, S.; Tamai, T.; Nakata, M.; Tatsuta, K.; Kinoshita, M. J. Am. Chem. Soc. 1995, 117, 3717-3727 and references cited within. (k) Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960-962. (l) Crich, D.; Ritchie, T. J. J. Chem. Soc., Chem. Commun. 1988, 1461-1463.
14. Aureolic acid antibiotics: (f) Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954-958. (g) Thiem, J.; Gerkeno, M.; Schottmer, B.; Weigand, J. Carbohydr Res. 1987, 164, 327-341. (h) Thiem, J.; Meyer, B. Tetrahedron 1981, 37, 551-558. (i) Roush, W. R.; Lin, X.-F. J. Am Chem. Soc. 1995, 117, 2236-2250 and references cited within. (j) Toshima, K.; Nozaki, Y ; Mukaiyama, S.; Tamai, T.; Nakata, M.; Tatsuta, K.; Kinoshita, M. J. Am. Chem. Soc. 1995, 117, 3717-3727 and references cited within. (k) Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960-962. (l) Crich, D.; Ritchie, T. J. J. Chem. Soc., Chem. Commun. 1988, 1461-1463.
15. Aureolic acid antibiotics: (f) Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954-958. (g) Thiem, J.; Gerkeno, M.; Schottmer, B.; Weigand, J. Carbohydr Res. 1987, 164, 327-341. (h) Thiem, J.; Meyer, B. Tetrahedron 1981, 37, 551-558. (i) Roush, W. R.; Lin, X.-F. J. Am Chem. Soc. 1995, 117, 2236-2250 and references cited within. (j) Toshima, K.; Nozaki, Y ; Mukaiyama, S.; Tamai, T.; Nakata, M.; Tatsuta, K.; Kinoshita, M. J. Am. Chem. Soc. 1995, 117, 3717-3727 and references cited within. (k) Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960-962. (l) Crich, D.; Ritchie, T. J. J. Chem. Soc., Chem. Commun. 1988, 1461-1463.
16. Aureolic acid antibiotics: (f) Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954-958. (g) Thiem, J.; Gerkeno, M.; Schottmer, B.; Weigand, J. Carbohydr Res. 1987, 164, 327-341. (h) Thiem, J.; Meyer, B. Tetrahedron 1981, 37, 551-558. (i) Roush, W. R.; Lin, X.-F. J. Am Chem. Soc. 1995, 117, 2236-2250 and references cited within. (j) Toshima, K.; Nozaki, Y ; Mukaiyama, S.; Tamai, T.; Nakata, M.; Tatsuta, K.; Kinoshita, M. J. Am. Chem. Soc. 1995, 117, 3717-3727 and references cited within. (k) Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960-962. (l) Crich, D.; Ritchie, T. J. J. Chem. Soc., Chem. Commun. 1988, 1461-1463.
17. Aureolic acid antibiotics: (f) Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954-958. (g) Thiem, J.; Gerkeno, M.; Schottmer, B.; Weigand, J. Carbohydr Res. 1987, 164, 327-341. (h) Thiem, J.; Meyer, B. Tetrahedron 1981, 37, 551-558. (i) Roush, W. R.; Lin, X.-F. J. Am Chem. Soc. 1995, 117, 2236-2250 and references cited within. (j) Toshima, K.; Nozaki, Y ; Mukaiyama, S.; Tamai, T.; Nakata, M.; Tatsuta, K.; Kinoshita, M. J. Am. Chem. Soc. 1995, 117, 3717-3727 and references cited within. (k) Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960-962. (l) Crich, D.; Ritchie, T. J. J. Chem. Soc., Chem. Commun. 1988, 1461-1463.
18. Aureolic acid antibiotics: (f) Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954-958. (g) Thiem, J.; Gerkeno, M.; Schottmer, B.; Weigand, J. Carbohydr Res. 1987, 164, 327-341. (h) Thiem, J.; Meyer, B. Tetrahedron 1981, 37, 551-558. (i) Roush, W. R.; Lin, X.-F. J. Am Chem. Soc. 1995, 117, 2236-2250 and references cited within. (j) Toshima, K.; Nozaki, Y ; Mukaiyama, S.; Tamai, T.; Nakata, M.; Tatsuta, K.; Kinoshita, M. J. Am. Chem. Soc. 1995, 117, 3717-3727 and references cited within. (k) Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960-962. (l) Crich, D.; Ritchie, T. J. J. Chem. Soc., Chem. Commun. 1988, 1461-1463.
19. Enediyne antibiotics: (m) Halcomb, R. L.; Wittman, M. D.; Olson, S. H.; Danishefsky, S. J.; Golik, J.; Wong, H.; Vyas, D. J. Am. Chem. Soc. 1991, 173, 5080-5082. (n) Nicolaou, K. C.; Groneberg, R D. J. Am. Chem. Soc. 1990, 112, 4085-4086. (o) Nicolaou, K. C.; Groneberg, R. D.; Miyazaki, T.; Sylianides, N. A.; Schuze, T. J.; Stahl, W. J. Am. Chem. Soc. 1990, 112, 8193-8195. (p) Kim, S.-H.; Augeri, D.; Yang, D.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 1766-1775 and references cited within. (q) Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749 and references cited within.
20. Enediyne antibiotics: (m) Halcomb, R. L.; Wittman, M. D.; Olson, S. H.; Danishefsky, S. J.; Golik, J.; Wong, H.; Vyas, D. J. Am. Chem. Soc. 1991, 173, 5080-5082. (n) Nicolaou, K. C.; Groneberg, R D. J. Am. Chem. Soc. 1990, 112, 4085-4086. (o) Nicolaou, K. C.; Groneberg, R. D.; Miyazaki, T.; Sylianides, N. A.; Schuze, T. J.; Stahl, W. J. Am. Chem. Soc. 1990, 112, 8193-8195. (p) Kim, S.-H.; Augeri, D.; Yang, D.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 1766-1775 and references cited within. (q) Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749 and references cited within.
21. Enediyne antibiotics: (m) Halcomb, R. L.; Wittman, M. D.; Olson, S. H.; Danishefsky, S. J.; Golik, J.; Wong, H.; Vyas, D. J. Am. Chem. Soc. 1991, 173, 5080-5082. (n) Nicolaou, K. C.; Groneberg, R D. J. Am. Chem. Soc. 1990, 112, 4085-4086. (o) Nicolaou, K. C.; Groneberg, R. D.; Miyazaki, T.; Sylianides, N. A.; Schuze, T. J.; Stahl, W. J. Am. Chem. Soc. 1990, 112, 8193-8195. (p) Kim, S.-H.; Augeri, D.; Yang, D.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 1766-1775 and references cited within. (q) Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749 and references cited within.
22. Enediyne antibiotics: (m) Halcomb, R. L.; Wittman, M. D.; Olson, S. H.; Danishefsky, S. J.; Golik, J.; Wong, H.; Vyas, D. J. Am. Chem. Soc. 1991, 173, 5080-5082. (n) Nicolaou, K. C.; Groneberg, R D. J. Am. Chem. Soc. 1990, 112, 4085-4086. (o) Nicolaou, K. C.; Groneberg, R. D.; Miyazaki, T.; Sylianides, N. A.; Schuze, T. J.; Stahl, W. J. Am. Chem. Soc. 1990, 112, 8193-8195. (p) Kim, S.-H.; Augeri, D.; Yang, D.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 1766-1775 and references cited within. (q) Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749 and references cited within.
23. Enediyne antibiotics: (m) Halcomb, R. L.; Wittman, M. D.; Olson, S. H.; Danishefsky, S. J.; Golik, J.; Wong, H.; Vyas, D. J. Am. Chem. Soc. 1991, 173, 5080-5082. (n) Nicolaou, K. C.; Groneberg, R D. J. Am. Chem. Soc. 1990, 112, 4085-4086. (o) Nicolaou, K. C.; Groneberg, R. D.; Miyazaki, T.; Sylianides, N. A.; Schuze, T. J.; Stahl, W. J. Am. Chem. Soc. 1990, 112, 8193-8195. (p) Kim, S.-H.; Augeri, D.; Yang, D.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 1766-1775 and references cited within. (q) Halcomb, R. L.; Boyer, S. H.; Wittman, M. D.; Olson, S. H.; Denhart, D. J.; Liu, K. K. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5720-5749 and references cited within.
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