Asymmetric synthesis of the polyol subunit of the macrolide antibiotic, ossamycin: A unique approach utilizing stereochemical specificity

Bulletin of the Chemical Society of Japan

Volumn 79, Issue 3, 2006, Pages 468-478

  Kutsumura, Noriki ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON-CHAIN ELONGATION; STEREOSELECTIVE CONDITIONS; STERIC HINDRANCE;

ANTIBIOTICS; GLUCOSE; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALCOHOLS;

1 ACETOXY 8 T BUTYLDIPHENYLSILOXY 1 [TETRAHYDRO 3 METHOXY 4 METHYLFURAN 2 YL] 2 METHYLOCTAN 2 OL; 12 T BUTYLDIPHENYLSILOXY 3 METHOXY 2,6 DIMETHYLDODECANE 1,4,5,6 TETROL; 2 [3 [2 (METHOXYCARBONYL)VINYL] 3 METHYLOXIRAN 2 YL] 4,5 BIS(BENZYLOXY) 12 T BUTYLDIPHENYLSILOXY 6 TRIETHYLSILOXY 6 METHYLDODECAN 3 YL DIMETHYLCARBAMATE; 2,3 BIS(BENZYLOXY) 10 T BUTYLDIPHENYLSILOXY 4 METHYLDECANE 1,4 DIOL; 2,3 BIS(BENZYLOXY) 10 T BUTYLDIPHENYLSILOXY 4 TRIETHYLSILOXY 4 METHYLDECANAL; 3,4 BIS(BENZYLOXY)TETRAHYDRO 5 METHOXY 2 METHYL 2 VINYLFURAN; 4 [2,3 BIS(BENZYLOXY) 10 T BUTYLDIPHENYLSILOXY 4 TRIETHYLSILOXY 1 HYDROXY 4 METHYLDECYL] 1,3 DIOXOLAN 2 ONE; 4,5 BIS(BENZYLOXY) 12 T BUTYLDIPHENYLSILOXY 6 TRIETHYLSILOXY 2,3 DIHYDROXY 6 METHYLDODECANOATE; 4,5 BIS(BENZYLOXY) 12 T BUTYLDIPHENYLSILOXY 6 TRIETHYLSILOXY 2,6 DIMETHYLDODECANE 1,3 DIOL; 4,5 BIS(BENZYLOXY) 12 T BUTYLDIPHENYLSILOXY 6 TRIETHYLSILOXY 3 (4 METHOXYBENZYLOXY) 2,6 DIMETHYLDODECAN 1 OL; 6,7 BIS(BENZYLOXY) 14 T BUTYLDIPHENYLSILOXY 8 TRIETHYLSILOXY 5 (4 METHYOXYBENZYLOXY) 2,4,8 TRIMETHYLTETRADEC 2 EN 1 OL; [3 [1,2 BIS(BENZYLOXY) 9 T BUTYLDIPHENYLSILOXY 3 TRIETHYLSILOXY 3 METHYLNONYL]OXIRAN 2 YL]METHANOL; [3 [4,5 BIS(BENZYLOXY) 12 T BUTYLDIPHENYLSILOXY 6 TRIETHYLSILOXY 3 (4 METHOXYBENZYLOXY) 6 METHYLDODECAN 2 YL] 2 METHYLOXIRAN 2 YL]METHANOL; [6 [3,4 BIS(BENZYLOXY)TETRAHYDRO 5 METHOXY 2 METHYLFURAN 2 YL]HEXYLOXY](T BUTYL)DIPHENYLSILANE; GLUCOSE; MACROLIDE; METHYL 2,3 DI O BENZYL 6 IODO 4 C METHYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 3 [3 [4,5 BIS(BENZYLOXY) 12 T BUTYLDIPHENYLSILOXY 6 TRIETHYLSILOXY 3 (4 METHOBENZYLOXY) 6 METHYLDODECAN 2 YL] 2 METHYLOXIRAN 2 YL]ACRYLATE; METHYL 4 [6 [1,2 BIS(BENZYLOXY) 9 T BUTYLDIPHENYLSILOXY 3 HYDROXY 3 METHYLNONYL] 5 METHYL 2 YL 2 OXO 1,3 DIOXAN 4 YL] 4 HYDROXYPENT 2 ENOATE; METHYL 4,5 BIS(BENZYLOXY) 12 T BUTYLDIPHENYLSILOXY 6 TRIETHYLSILOXY 6 METHYLDODEC 2 ENOATE; METHYL 6,7 BIS(BENZYLOXY) 14 T BUTYLDIPHENYLSILOXY 8 TRIETHYLSILOXY 5 (4 METHYOXYBENZYLOXY) 2,4,8 TRIMETHYLTETRADEC 2 ENOATE; OSSAMYCIN; POLYOL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; DRUG SYNTHESIS; EPOXIDATION; HYDROXYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 33750494117     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.468     Document Type: Article

References (35)

1. H. Schmitz, S. D. Jubinski, I. R. Hooper, K. E. Crook, Jr., K. E. Price, J. Lein, J. Antibiot. 1965, 18, 82.
2. H. A. Kirst, J. S. Mynderse, J. W. Martin, P. J. Baker, J. W. Paschal, J. L. Rios Steiner, E. Lobkovsky, J. Clardy, J. Antibiot. 1996, 49, 162.
3. a) T. Kihara, H. Kusakabe, G. Nakamura, T. Sakurai, K. Isono, J. Antibiot. 1981, 34, 1073.
4. b) T. Sakurai, T. Kihara, K. Isono, Acta Crystallogr., Sect. C 1983, 39, 295.
5. c) T. Kihara, K. Isono, J. Antibiot. 1983, 36, 1263.
6. d) T. Kihara, M. Ubukata, J. Uzawa, K. Isono, J. Antibiot. 1989, 42, 919.
7. a) J. W. Chamberlin, M. Gorman, A. Agtarap, Biochem. Biophys. Res. Commun. 1969, 34, 448.
8. b) W. F. Prouty, R. M. Thompson, H. K. Schnoes, F. M. Strong, Biochem. Biophys. Res. Commun. 1971, 44, 619.
9. c) M. Von Glehn, R. Norrestam, P. Kierkegaard, L. Maron, L. Ernster, FEBS Lett. 1972, 20, 267.
10. d) G. T. Carter, J. Org. Chem. 1986, 51, 4264.
11. e) K. Kobayashi, C. Nishino, J. Ohya, S. Sato, T. Mikawa, Y. Shiobara, M. Kodama, M. Nishimoto, J. Antibiot. 1987, 40, 1053.
12. H. A. Kirst, S. H. Larsen, J. W. Paschal, J. L. Occolowitz, L. C. Creemer, J. L. Rios Steiner, E. Lobkovsky, J. Clardy, J. Antibiot. 1995, 48, 990.
13. a) R. Q. Thompson, M. M. Hoehn, C. E. Higgins, Antimicrob. Agents Chemother. 1962, 6, 474.
14. b) V. D. Wuthier, W. Keller-Schierlein, Helv. Chim. Acta 1984, 67, 1206.
15. a) A. R. Salomon, D. W. Voehringer, L. A. Herzenberg, C. P. Khosla, Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 14766.
16. b) A. R. Salomon, D. W. Voehringer, L. A. Herzenberg, C. P. Khosla, Chem. Biol. 2001, 8, 71.
17. N. Kutsumura, S. Nishiyama, Tetrahedron Lett. 2005, 46, 5707.
18. K. Sato, K. Kubo, N. Hong, H. Kodama, J. Yoshimura, Bull. Chem. Soc. Jpn. 1982, 55, 938.
19. B. Bernet, A. Vasella, Helv. Chim. Acta 1979, 62, 1990.
20. A. Rodríguez, M. Nomen, B. W. Spur, J. J. Godfroid, Tetrahedron Lett. 1999, 40, 5161.
21. a) H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 5919.
22. b) H. C. Brown, K. S. Bhat, R. S. Randad, J. Org. Chem. 1989, 54, 1570.
23. a) D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737.
24. b) J. R. Gage, D. A. Evans, Org. Synth. 1989, 68, 83.
25. Z-Selective Horner-Wadsworth-Emmons reaction: K. Ando, J. Org. Chem. 1999, 64, 8406.
26. a) T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974.
27. b) Y. Gao, R. M. Hanson, J. M. Klumder, S. Y. Koo, H. Masamune, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765.
28. c) J. G. Hill, B. E. Rossiter, K. B. Sharpless, J. Org. Chem. 1983, 48, 3607.
29. d) K. B. Sharpless, T. R. Verhoeven, Aldrichimica Acta 1979, 12, 63.
30. a) M. R. Johnson, T. Nakata, Y. Kishi, Tetrahedron Lett. 1979, 20, 4343.
31. b) B. H. Lipshutz, R. S. Wilhelm, J. Kozlowski, Tetrahedron Lett. 1982, 23, 3755.
32. c) M. A. Tius, A. H. Fauq, J. Org. Chem. 1983, 48, 4131.
33. d) J. M. Chong, D. R. Cyr, E. K. Mar, Tetrahedron Lett. 1987, 28, 5009.
34. K. Maruyama, M. Ueda, S. Sasaki, Y. Iwata, M. Miyazawa, M. Miyashita, Tetrahedron Lett. 1998, 39, 4517.
35. F. Bravo, F. E. McDonald, W. A. Neiwert, B. Do, K. I. Hardcastle, Org. Lett. 2003, 5, 2123.