Regioselective ring opening of thiomalic acid anhydrides by carbon nucleophiles. Synthesis and X-ray structure elucidation of novel thiophenone derivatives

Tetrahedron

Volumn 65, Issue 18, 2009, Pages 3711-3716

  Kikionis, Stefanos ^a   McKee, Vickie ^b   Markopoulos, John ^c   Igglessi Markopoulou, Olga ^a  

^a NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF ATHENS   (Greece)

Author keywords

Mercaptosuccinic anhydride; Thiolactomycin; Thiolactone; Thiomalic anhydride; Thiophenone; Thiotetronic

Indexed keywords

ACID ANHYDRIDE; BENZENE DERIVATIVE; CARBENE; CARBON; NUCLEOPHILE; THIOLACTONE; THIOMALIC ACID; THIOPHENONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL BOND; CYCLIZATION; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 63049097511     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.081     Document Type: Article

References (30)

1. Oishi H., Noto T., Sasaki H., Suzuki K., Hayashi T., Okazaki H., Ando K., and Sawada M. J. Antibiot. 35 (1982) 391
2. Wang C.-L.J., and Salvino J.M. Tetrahedron Lett. 25 (1984) 5243
3. Noto T., Miyakawa S., Oishi H., Endo H., and Okazaki H. J. Antibiot. 35 (1982) 401
4. Kremer L., Douglas J.D., Baulard A.R., Morehouse C., Guy M.R., Alland D., Dover L.G., Lakey J.H., Jacobs W.R., Brennan P.J., Minnikin D.E., and Besra G.S. J. Biol. Chem. 275 (2000) 16857
5. Slayden R.A., Lee R.E., Armour J.W., Cooper A.M., Orme I.M., Brennan P.J., and Besra G.S. Antimicrob. Agents Chemother. 40 (1996) 2813
6. Kim P., Zhang Y.-M., Shenoy G., Nguyen Q.-A., Boshoff H.I., Manjunatha U.H., Goodwin M.B., Lonsdale J., Price A.C., Miller D.J., Duncan K., White S.W., Rock C.O., Barry III C.E., and Dowd C.S. J. Med. Chem. 49 (2006) 159
7. Ohata K., and Terashima S. Bioorg. Med. Chem. Lett. 17 (2007) 4070
8. Price A.C., Choi K.-H., Heath R.J., Li Z., White S.W., and Rock C.O. J. Biol. Chem. 276 (2001) 6551
9. Bhowruth V., Brown A.K., Senior S.J., Snaith J.S., and Besra G.S. Bioorg. Med. Chem. Lett. 17 (2007) 5643
10. Bhowruth V., Dover L.G., and Besra G.S. In: King F.D., and Lawton G. (Eds). Progress in Medicinal Chemistry Vol. 45 (2007), Elsevier, Amsterdam 169-203
11. Johanson P., Wiltschi B., Kumari P., Kessler B., Vonrhein C., Vonck J., Oesterhelt D., and Grininger M. PNAS 105 (2008) 12803-12808
12. McFadden J.M., Medghalchi S.M., Thupari J.N., Pinn M.L., Vadlamudi A., Miller K.I., Kuhajda F.P., and Townsend C.A. J. Med. Chem. 48 (2005) 946
13. Benary E. Ber. 43 (1910) 1943
14. Benary E. Ber. 46 (1913) 2103
15. O' Mant D.M. J. Chem. Soc., Perkin Trans. 1 (1968) 1501
16. Budnikova M.V., and Rubinov D.B. Russ. J. Org. Chem. 37 (2001) 1478
17. Chambers M.S., and Thomas E.J. J. Chem. Soc., Perkin Trans. 1 (1997) 417
18. Mc Fadden J.M., Frehywot G.L., and Townsend C.A. Org. Lett. 4 (2002) 3859
19. Jones S.M., Urch J.E., Kaiser M., Brun R., Harwood J.L., Berry C., and Gilbert I.H. J. Med. Chem. 48 (2005) 5932
20. Ohata K., and Terashima S. Tetrahedron Lett. 47 (2006) 2787
21. Ohata K., and Terashima S. Bioorg. Med. Chem. Lett. 18 (2008) 5598
22. Dormann K.L., and Brückner R. Angew. Chem., Int. Ed. 46 (2007) 1160
23. Shenoy G., Kim P., Goodwin M., Nguyen Q.-A., Barry C.E., and Dowd C.S. Heterocycles 63 (2004) 519
24. Petroliagi M., and Igglessi-Markopoulou O. Tetrahedron: Asymmetry 10 (1999) 1873
25. Mitsos C., Zografos A., and Igglessi-Markopoulou O. J. Org. Chem. 65 (2000) 5852
26. Athanasellis G., Igglessi-Markopoulou O., and Markopoulos J. Synlett (2002) 1736
27. Kikionis S., Prousis K.C., Detsi A., and Igglessi-Markopoulou O. ARKIVOC (2006) 28
28. Kikionis S., McKee V., Markopoulos J., and Igglessi-Markopoulou O. Tetrahedron 64 (2008) 5454
29. Fluka Catalogue; Buchs SG, 2008.
30. Sheldrick G.M. Acta Crystallogr. A64 (2008) 112