Studies on the synthesis of DNA-damaging part of leinamycin: Regioselectivity in Ti(OiPr)4 mediated opening of hydroxy epoxides with carboxylic acids

Tetrahedron

Volumn 61, Issue 31, 2005, Pages 7481-7488

  Nahmany, Moshe ^a   Melman, Artem ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Epoxide opening; Leinamycin; Sharpless epoxidation; Wittig Horner olefination

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; CARBOXYLIC ACID DERIVATIVE; DNA; EPOXIDE; GERANIOL; LEINAMYCIN; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; DNA DAMAGE; DRUG SYNTHESIS; ENANTIOMER; HORNER REACTION; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; RING OPENING; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 21744434931     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.050     Document Type: Article

References (29)

1. M. Hara, I. Takahashi, M. Yoshida, K. Asano, I. Kawamoto, M. Morimoto, and H. Nakano J. Antibiot. 42 1989 333 335
2. M. Hara, Y. Saitoh, and H. Nakano Biochemistry 29 1990 5676 5681
3. M. Hara, K. Asano, I. Kawamoto, T. Takiguchi, S. Katumata, K. Takahashi, and H. Nakano J. Antibiot. 42 1989 1768 1774
4. A. Asai, M. Hara, S. Kakita, Y. Kanda, M. Yoshida, H. Saito, and Y. Saitoh J. Am. Chem. Soc. 118 1996 6802 6803
5. K. Mitra, W. Kim, J.S. Daniels, and K.S. Gates J. Am. Chem. Soc. 119 1997 11691 11692
6. L. Breydo, H. Zang, and K.S. Gates Tetrahedron Lett. 45 2004 5711 5716
7. Y. Kanda, T. Ashizawa, S. Kakita, Y. Takahashi, M. Kono, M. Yoshida, Y. Saitoh, and M. Okabe J. Med. Chem. 42 1999 1330 1332
8. W.A. Denny Curr. Med. Chem. 8 2001 533 544
9. Y. Kanda, and T. Fukuyama J. Am. Chem. Soc. 115 1993 8451 8452
10. T. Chatterji, M. Kizil, K. Keerthi, G. Chowdhury, T. Pospísil, and K.S. Gates J. Am. Chem. Soc. 119 1997 11691 11692
11. A.H.F. Lee, J. Chen, A.S.C. Chan, and T. Li Phosphorus, Sulfur Siliicon Relat. Elem. 178 2003 1163 1174
12. R. Salvetti, G. Martinetti, D. Ubiali, M. Pregnolato, and G. Pagani Farmaco 58 2003 995 998
13. M. Kodama, H. Minami, Y. Mima, and Y. Fukuyama Tetrahedron Lett. 31 1990 4025 4026
14. L. Poppe, L. Novák, P. Kolonits, A. Bata, and C. Szántay Tetrahedron 44 1988 1477 1487
15. X. Liao, and X. Xu Tetrahedron Lett. 41 2000 4641 4644
16. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5165 5180
17. S. Terao, M. Shirashi, and K. Kato Synthesis 1979 467 468
18. Chiral racemic and non-racemic compounds are identified by R/S names only according to Sharpless oxidation product.
19. M. Caron, and K.B. Sharpless J. Org. Chem. 50 1985 1560 1563
20. For example: F.E. McDonald, K.B. Reddy, and Y. Díaz J. Am. Chem. Soc. 122 2000 4304 4309
21. D. Seebach, E. Hungerbuehler, R. Naef, P. Schnurrenberger, B. Weidmann, and M. Zueger Synthesis 1982 138
22. D. Seebach, B. Weidmann, and L. Widler R. Scheffold Modern synthetic methods 1983 Sauerlaender Aarau 217
23. T. Momose, M. Setoguchi, T. Fujita, H. Tamura, and N. Chida Chem. Commun. 2000 2237 2238
24. E. Falb, T. Yechezkel, Y. Salitra, and C. Gilon J. Pept. Res. 53 1999 507 517
25. M. Nahmany, and A. Melman Org. Lett. 3 2001 3733 3735
26. G.R. Weihe, and T.C. Mcmorris J. Org. Chem. 43 1978 3942
27. H.-G. Lehmann, and R. Weichert Angew. Chem., Int. Ed. Engl. 7 1968 300 301
28. A. Nangia, and R.P. Bheema Tetrahedron Lett. 33 1992 2375 2378
29. M.A. Blanchette, W. Choy, J.T. Davis, A.P. Essenfeld, S. Masamune, W.R. Roush, and T. Sakai Tetrahedron Lett. 25 1984 2183 2186