Novel concise synthesis of (±)-noviose and L-(+)-noviose by palladium-catalyzed epoxide opening

Synthesis

Volumn , Issue 8, 2011, Pages 1290-1294

  Matsushima, Yoshitaka ^a   Kino, Jun ^a  

^a HAMAMATSU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

aminocoumarin antibiotics; Noviose; novobiocin; palladium catalyzed epoxide opening

Indexed keywords

AMINOCOUMARIN ANTIBIOTICS; CHIRAL EPOXIDES; CONCISE SYNTHESIS; DEOXY SUGAR; KEY REACTIONS; NOVIOSE; NOVOBIOCIN; OPENING REACTIONS; SYNTHETIC ROUTES;

ANTIBIOTICS; SUGARS; SYNTHESIS (CHEMICAL);

CATALYSIS;

4 METHOXY 5,5 DIMETHYLHEX 2 EN 5 OLIDE; CLOROBIOCIN; COUMAMYCIN A1; EPOXIDE; ETHYL 4,5 EPOXY 5 METHYLHEX 2 ENOATE; ETHYL 5 HYDROXY 4 METHOXY 5 METHYLHEX 2 ENOATE; LEVO NOVIOSE [6 DEOXY 5 C METHYL,4 O METHYL LEVO LYXO HEXOPYRANOSE 1]; METHYL 5 HYDROXY 4 METHOXY 5 METHYLHEX 2 ENOATE; NOVIOSE; NOVIOSE [6 DEOXY 5 C METHYL,4 O METHYL DEXTRO LYXO HEXOPYRANOSE 1]; NOVOBIOCIN; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; LACTONIZATION; NONHUMAN; NUCLEOPHILICITY; SUBSTITUTION REACTION;

EID: 79953797089     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258475     Document Type: Article

References (33)

1. Weymouth-Wilson A C., Nat. Prod. Rep. 1997 14 99
2. Paloma L G., Smith J A., Chazin W J., Nicolaou K C., J. Am. Chem. Soc. 1994 116 3697
3. Nedal A, Zotchev S B., Appl. Microbiol. Biotechnol. 2004 64 7
4. Matsushima Y, Kino J, Tetrahedron Lett. 2005 46 8609
5. Matsushima Y, Kino J, Tetrahedron Lett. 2006 47 8777
6. Matsushima Y, Kino J, Tetrahedron 2008 64 3943
7. Matsushima Y, Kino J, Eur. J. Org. Chem. 2010 2206
8. For the latest review on novobiocin related aminocoumarins, see:, Heide L, Biotechnol. Adv. 2009 27 1006
9. Garca I G., Stevenson C E. M., Usn I, Meyers C F. L., Walsh C T., Lawson D M., J. Mol. Biol. 2010 395 390
10. Donnelly A, Blagg B S. J., Cur. Med. Chem. 2008 15 2702
11. Vaterlaus B P., Kiss J, Spiegelberg H, Helv. Chim. Acta 1964 47 381
12. Kiss J, Spiegelberg H, Helv. Chim. Acta 1964 47 398
13. Klemer A, Waldmann M, Liebigs Ann. Chem. 1986 221
14. Laurin P, Ferroud D, Klich M, Dupuis-Hamelin C, Mauvais P, Lassaigne P, Bonnefoy A, Musicki B, Bioorg. Med. Chem. Lett. 1999 9 2079
15. Periers A.-M, Laurin P, Benedetti Y, Lachaud S, Ferroud D, Iltis A, Haesslein J.-L, Klich M, L'Hermite G, Musicki B, Tetrahedron Lett. 2000 41 867
16. Takeuchi M, Taniguchi T, Ogasawara K, Tetrahedron Lett. 2000 41 2609
17. Gammon D W., Hunter R, Wilson S, Tetrahedron Lett. 2002 43 3141
18. Jeelnik M, Leban I, Polanc S, Koevar M, Org. Lett. 2003 5 2651
19. Hanessian S, Auzzas L, Org. Lett. 2008 10 261
20. He Y, Xue J, Zhou Y, Yang J, Yu X, Tetrahedron Lett. 2009 50 2317; this is the latest paper, however, l -(+)-noviose was reported as a by-product during the synthesis of noviose 1,2-acetonide by the modified route given in references 11d and 11e
21. Pankau W M., Kreiser W, Helv. Chim. Acta 1998 81 1997
22. Pankau W M., Kreiser W, Tetrahedron Lett. 1998 39 2089
23. Yu X M., Shen G, Blagg B S. J., J. Org. Chem. 2004 69 7375
24. Reddy D S., Srinivas G, Rajesh B M., Kannan M, Rajale T V., Iqbal J, Tetrahedron Lett. 2006 47 6373
25. Donnelly A, Zhao H, Kusuma B R., Blagg B S. J., Med. Chem. Commun. 2010 1 165
26. During our course of pursuing the effective synthesis of osmundalactones, an appealing method for the -lactoniza-tion accompanied by trans - cis isomerization was reported:, Ono M, Zhao X Y., Shida Y, Akita H, Tetrahedron 2007 63 10140
27. Yu X.-Q, Yoshimura F, Ito F, Sasaki M, Hirai A, Tanino K, Miyashita M, Angew. Chem. Int. Ed. 2008 47 750
28. 3): = 166.1, 143.1, 124.4, 62.1, 61.7, 51.7, 24.6, 18.6
29. 3): = 167.7, 146.2, 141.0, 123.7, 118.6, 60.1, 26.5, 18.9, 14.3
30. Marschall H, Penninger J, Weyerstahl P, Liebigs Ann. Chem. 1982 49
31. Uchida K, Ishigami K, Watanabe H, Kitahara T, Tetrahedron 2007 63 1281
32. Nagumo S, Nakano T, Hata K, Mizukami M, Miyashita M, Org. Lett. 2010 12 908
33. Achmatowicz O Jr., Grynkiewicz G, Szechner B, Tetrahedron 1976 32 1051 This article was occasionally quoted as the reference for the synthesis of ()-noviose by mistake, which, however, certainly includes H NMR data of synthesized methyl dl -novioside along with those of naturally derived noviose.