Selective photochemical cleavage of an α-ketoamide in a highly functionalised macrolide ascomycin

Tetrahedron Letters

Volumn 45, Issue 12, 2004, Pages 2527-2530

  Bulusu, Murty A R C ^a   Waldstätten, Peter ^a   Tricotett, Thomas ^a   Schulz, Gerhard ^a  

^a Novartis Inst for Biomed Research   (Austria)

Author keywords

Photochemical amide cleavage; Phototransformation; Zwitterion

Indexed keywords

AMIDE; ASCOMYCIN; MACROLIDE; METHOXY 9 HYDROXYASCOMYCIN; METHOXYASCOMYCIN; PIMECROLIMUS; PIPECOLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SELECTIVITY; DRUG SYNTHESIS; FERMENTATION TECHNIQUE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SAPONIFICATION;

EID: 1542302468     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.014     Document Type: Article

References (29)

1. Arai T., Koyoma Y., Suenaga T., Honda H. J. Antibiot. Ser. A. 15:1962;231-232.
2. Hatanaka H., Iwami M., Kino T., Goto T., Okuhara M. J. Antibiot. 41:1988;1586-1591.
3. Hatanaka H., Kino T., Miyata S., Inamura N., Kuroda A., Goto T., Tanaka H., Okuhara M. J. Antibiot. 41:1988;1592-1601.
4. Morisaki M., Arai T. J. Antibiot. 45:1992;126-128.
5. Meingassner J., Grassberger M., Fahrngruber H., Moore H.D., Schuurman H., Stütz A. Br. J. Dermatol. 137:1997;568-576.
6. Grassberger M., Baumruker T., Enz A., Hiestand P., Hultsch T., Kalthoff F., Schuler W., Schulz M., Werner F.-J., Winiski A., Wolff B., Zenke G. Br. J. Dermatol. 141:1999;264-273.
7. Stütz A., Grassberger M., Meingassner J.G. Semin. Cutaneous Med. Surg. 20:2001;233-241.
8. Hebert A., Warken K.A., Cherill R. Semin. Cutaneous Med. Surg. 20:2001;260-267.
9. Wellington K., Jarvis B. Drugs. 62:2002;817-840.
10. Grassberger M., Meingassner J., Stütz A., Rappersberger K., Wolff K. Ascomycins. Roenigk H.H., Maibach H.I. Psoriasis. 3rd ed. 1998;769-779 Marcel Dekker, New York, Basel, Hong Kong. Chapter 66.
11. Rappersberger K., Komar M., Ebelin M.E., Scott G., Burtin P., Greig G., Kehren J., Chibout S.D., Holter W., Richter L., Oberbauer R., Cordier A., Stütz A., Wolff K. J. Invest. Dermatol. 119:2002;876-888.
12. Kapp A., Papp K., Bingham A., Fölster-Holst R., Ortonne J.P., Potter P., Gulliver W., Paul C., Molloy S., Barbier N., Hultsch T., de Prost Y. J. Allergy Clin. Immunol. 110:2002;277-284.
13. Meurer M., Fölster-Holst R., Wozel G., Weidinger G., Jünger M., Bräutigam M. Dermatology. 205:2002;271-277.
14. Wahn U., Bos J.D., Goodfield M., Caputo R., Papp K., Manjra A., Dobozy A., Paul C., Molloy S., Graeber M., Cherill R., DeProst Y. Pediatrics. 110:2002;e2.
15. Ho V., Gupta A., Kaufmann R., Todd G., Vanachlocha F., Takaoka R., Fölster-Holst R., Potter P., Marshall K., Thurston M., Bush C., Cherill R. J. Pediatr. 142:2003;155-162.
16. VanDuyne G.D., Standaert R.F., Karplus P.A., Schreiber S.L., Clardy J. Science. 252:1991;839-842.
17. Askin D., Reamer R.A., Joe D., Volante R.P., Shinkai I. J. Org. Chem. 55:1990;5448-5450.
18. Askin D., Joe D., Reamer R.A., Volante R.P., Shinkai I. J. Org. Chem. 55:1990;5451-5454.
19. Bulusu A.R.C.M., Haidl E.H., Schulz G., Waldstaetten P., Grassberger M. Indian J. Chem. 38B:1999;1159-1164.
20. Bulusu A. EP 0626385A. 1994;Sandoz Ltd.
21. Bulusu A.R.C.M., Waldstätten P., Schulz G., Grassberger M. Tetrahedron Lett. 45:2004;2523.
22. Chesta C.A., Whitten D.G. J. Am. Chem. Soc. 114:1992;2188-2197.
23. Aoyama H., Hasegawa T., Watabe M., Shiraishi H., Omote Y. J. Org. Chem. 43:1978;419-422.
24. Aoyama H., Sakamoto M., Kuwabara K., Yoshida K., Omote Y. J. Am. Chem. Soc. 105:1983;1958-1964.
25. Aoyama H., Hasegawa T., Omote Y. J. Am. Chem. Soc. 101:1979;5343-5347.
26. 1H-decoupling experiments.
27. Horvath, A. Ph.D. Thesis, University of Vienna, 1993
28. Guibe F., Saint M'Leux Y. Tetrahedron Lett. 22:1981;3591-3594.
29. Olah G.A., Narang S.C., Gupta B.G.B., Malhotra R. J. Org. Chem. 44:1979;1247-1251.