Synthesis of (-)-hygromycin a: application of mitsunobu glycosylation and tethered aminohydroxylation

Angewandte Chemie - International Edition

Volumn 48, Issue 35, 2009, Pages 6507-6510

  Donohoe, Timothy J ^a   Flores, Aida ^a   Bataille, Carole J R ^a   Churruca, Fátima ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Aminohydroxylation; Mitsunobu glycosylation; Natural products; Total synthesis

Indexed keywords

AMINOCYCLITOLS; AMINOHYDROXYLATION; HYGROMYCIN; KEYPOINTS; KINETIC STABILITY; MITSUNOBU GLYCOSYLATION; NATURAL PRODUCTS; PROTECTING GROUP; SUGAR UNITS; TETHERED AMINOHYDROXYLATION; TOTAL SYNTHESIS;

AVIATION; ESTERIFICATION; GLYCOSYLATION; SUGAR (SUCROSE); SUGARS;

HYDROXYLATION;

ANTIINFECTIVE AGENT; CINNAMIC ACID DERIVATIVE; DRUG DERIVATIVE; HYGROMYCIN; HYGROMYCIN B;

ARTICLE; CHEMISTRY; GLYCOSYLATION; STREPTOMYCES; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CINNAMATES; GLYCOSYLATION; HYGROMYCIN B; STREPTOMYCES;

EID: 70349924966     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902840     Document Type: Article

References (30)

1. a) R. C. Pittenberger, R. N. Wolfe, M. M. Hohen, P. N. Marks, W. A. Daily, M. McGuire, Antibiot. Chemother. 1953, 3, 1268;
2. b) R. L. Mann, R. M. Gale, F. R. VanAbeele, Antibiot. Chemother. 1953, 3, 1279;
3. c) Y. Sumiki, G.Nakamura, M. Kawasaki, S. Yamashita, K. Anazi, K. Isono, Y. Serizawa, Y. Tomiyama, S. Suzuki, J.Antibiot. Ser. A 1955, 8, 170;
4. d) K. Isono, S. Yamashita, Y.Tomiyama, S. Suzuki, J.Antibiot. 1957, 10, 21;
5. e) Y.Wakisaka, K. Koizumi, Y. Nishimoto, M. Kobayashi, N.Tsuji, J. Antibiot. 1980, 33, 695;
6. f) M. Uyeda, M. Mizukami, K. Yokomizo, K. Suzuki, Biosci. Biotechnol. Biochem. 2001, 65, 1252.
7. M. C. Guerrer, J. Modolell, Eur. J. Biochem. 1980, 107, 409.
8. a) S. J. Hecker, M. L. Minich, K. M. Werner, Bioorg. Med. Chem. Lett. 1992, 2, 533;
9. b) S. J. Hecker, S. C. Lilley, M. L. Minich, K. M. Werner, Bioorg. Med. Chem. Lett. 1992, 2, 1015;
10. c) S. J. Hecker, S. C. Lilley, K. M. Werner, Bioorg. Med. Chem. Lett. 1992, 2, 1043;
11. d) S.J. Hecker, C.B. Cooper, K. T Blair, S. C. Lilley, M. L. Minich, K. M. Werner, Bioorg. Med. Chem. Lett. 1993, 3, 289;
12. e) C. B. Cooper, K. T. Blair, C. S. Iones, M. L. Minich, Bioorg. Med. Chem. Lett. 1997, 7, 1747;
13. f) S. Omura, A. Hakagawa, T. Fujimoto, K. Saito, K. Otoguro, J. Antibiot. 1987, 40, 1619;
14. g) A. Nakagawa, T. Fujimoto, S. Omura, J. C. Walsh, R. L. Stoish, B. George, J. Antibiot. 1987, 40, 1627.
15. a) N. Chida, M. Ohtsuka, K. Nakazawa, S. Ogawa, J. Chem. Soc. Chem. Commun. 1989, 436;
16. b) N. Chida, M. Ohtsuka, K. Nakazawa, S. Ogawa, J. Org. Chem. 1991, 56, 2976.
17. a) B. M. Trost, J. Dudash, O. Dirat, Chem. Eur. J.2002, 5, 259;
18. b) B. M. Trost, J. Dudash, E. J. Hembre, Chem. Eur. J.2001, 7, 1619.
19. a) T. J. Donohoe, P. D Iohnson, R. J. Pye, M. Keenan, Org. Lett. 2005, 7, 1275-1277;
20. b) T.J. Donohoe, C.J.R. Bataille, W. Gattrell, J. Kloesges, E. Rossignol, Org. Lett. 2007, 9, 1725-1728.
21. Hygromycin A itself is isolated together with its epimer at this position, see Ref. [1e].
22. a) A. B. Smith III, K. J. Hale, R. A. Rivero, Tetrahedron Lett. 1986, 27, 5813;
23. b) A. B. Smith III, R. A. Rivero, K. J. Hale, H. A. Vaccaro, J.Am. Chem. Soc. 1991, 113, 2092;
24. c) W R. Roush, X. F. Lin, J. Org. Chem. 1991, 56, 5740;
25. d) for early work see, G. Grynkiewicz, Carbohydr. Res. 1977, 53, C11.
26. For a review see: T. J. Donohoe, T. J. C. O'Riordan, C. P. Rosa, Angew. Chem. 2009, 121, 1032-1035;
27. Angew. Chem. Int. Ed. 2009, 48, 1014-1017.
28. J.D Stevens, H. G. Fletcher, J.Org. Chem. 1968, 33, 1799.
29. M. Node, K. Nishide, M. Sai, K. Fuji, E. Fujita, J.Org. Chem. 1981, 46, 1991.
30. K. A. Scheidt, H. Chen, B.C. Follows, S. R. Chemler, D. S. Coffey, W. R. Roush, J. Org. Chem. 1998, 63, 6436.