A remarkably facile and stereochemically controlled fragmentation reaction in the hygrolide group of macrolide antibiotics

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9001-9004

  Hanessian, Stephen ^a   Tehim, Ashok ^a   Meng, Qingchang ^a   Granberg, Kenneth ^b  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BAFILOMYCIN; MACROLIDE;

ARTICLE; CHEMICAL REACTION; DRUG CONFORMATION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030577489     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02113-2     Document Type: Article

References (22)

1. 1. a) Werner, G.; Hagenmaier, H.; Drautz, H.; Baumgartner, A.; Zährner, H. J. Antibiotics 1984, 37, 110;
2. b) Kretschmer, A.; Dorgerloh, M.; Deeg, M.; Hagenmaier, H. Agr. Biol. Chem. 1985, 49, 2509;
3. c) Seto, H.; Akao, H.; Furihata, K.; Otake, N. Tetrahedron Lett. 1982, 23, 2667;
4. d) Hensens, O.D.; Monaghan, R.L.; Huang, L.; Albers-Schönberg, G. J. Am. Chem. Soc. 1983, 105, 3672;
5. e) Goetz, M.A.; McCormick, P.A.; Monaghan, R.L.; Ostlind, D.A.; Hensens, O.D.; Liesch, J.M.; Albers-Schönberg, G. J. Antibiotics 1985, 38, 164;
6. f) Wilton, J.H; Hokanson, G.C.; French, J.C. J. Antibiotics 1985, 38, 1449.
7. 2. a) Dröse, S.; Bindseil, K.U.; Bowman, E.J.; Siebers, A.; Zeeck, A.; Altendorf, K. Biochemistry 1993, 32, 3902;
8. b) Bownan, E.J.; Siebers, A.; Attendorf, K. Proc. Natl. Sci. USA 1988, 85, 7972;
9. c) Sundquist, K.; Lakkakorpi, P.; Wallmark, B.; Väänäen, K. Biochem. Biophys. Res. Commun. 1990, 168, 309.
10. 3. 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, 25, 5565.
11. 4. a) Baker, G.H.; Brown, P.J.; Dorgan, J.J.; Everett, J.R. J. Chem. Soc. Perkin Trans II 1989, 1073;
12. b) Corey, E.J.; Ponder, J.W. Tetrahedron Lett. 1984, 25, 4325.
13. 5. a) Kinashi, H.; Someno, K.; Sakaguchi, K. Tetrahedron Lett. 1981, 22, 3861;
14. b) Bindseil, K.U.; Zeeck, A. J. Org. Chem. 1993, 58, 5487.
15. 6. Deeg, M.; Hagenmaier, H.; Kretschmer, A. J. Antibiotics 1987, 40, 320.
16. 7. Hanessian, S.; Meng, Q.; Olivier, E. Tetrahedron Lett. 1994, 35, 5393.
17. 8. Mitsunobu, O. Synthesis 1981, 1.
18. 9. a) Grob, C.A.; Baumann, W. Helv. Chim. Acta 1955, 38, 594;
19. b) Grob, C.A. Angew. Chem. Int. Ed. Engl. 1969, 8, 535;
20. c) Grob, C.A.; Schiess, P.W. Angew. Chem. Int. Ed. Engl. 1967, 6, 1.
21. 10. For related examples, see Hesse, M. "Ring Enlargement in Organic Chemistry", VCH Publishers, Weinheim 1991, Chapter 8.
22. 11. All new compounds were adequately characterized by analytical and spectroscopic methods. Melting points are uncorrected.