Toward a total synthesis of an aglycone of spiramycine; two complementary accesses to a C-5C-9 fragment

作者: G Oddon , D Uguen

DOI: 10.1016/S0040-4039(97)00945-3

关键词:

摘要: Abstract Both homochiral acetates 4d and 5f , which were obtained by lipase-catalysed acetylation of either the tetraol 4a or diol 5e respectively, have been converted stereoconvergently into a C -5 -9 fragment title antibiotic.

参考文章(7)
Gary E. Keck, Anandan Palani, Stanton F. McHardy, Total Synthesis of (+)-Carbonolide B Journal of Organic Chemistry. ,vol. 59, pp. 3113- 3122 ,(1994) , 10.1021/JO00090A032
Kuniaki Tatsuta, Yoshiya Amemiya, Shunji Maniwa, Mitsuhiro Kinoshita, Total synthesis of carbomycin B and josamycin (leucomycin A3) Tetrahedron Letters. ,vol. 21, pp. 2837- 2840 ,(1980) , 10.1016/S0040-4039(00)78621-7
ERNEST L. ELIEL, PHILIP H. WILKEN, FABIAN T. FANG, Racemization of Phenylalkanes in Presence of Lewis Acids Journal of Organic Chemistry. ,vol. 22, pp. 231- 234 ,(1957) , 10.1021/JO01354A001
P. Breuilles, T. Schmittberger, D. Uguen, The double-meso trick Tetrahedron Letters. ,vol. 34, pp. 4205- 4208 ,(1993) , 10.1016/S0040-4039(00)60528-2
K. C. Nicolaou, M. R. Pavia, S. P. Seitz, Synthesis of 16-membered-ring macrolide antibiotics. 4. Carbomycin B and leucomycin A3: total synthesis of cyclic key intermediate Journal of the American Chemical Society. ,vol. 103, pp. 1224- 1226 ,(1981) , 10.1021/JA00395A044
Noriyuki NAKAJIMA, Kouichi UOTO, Osamu YONEMITSU, Tadashi HATA, Facile Total Synthesis of Carbonolides by Witting-Hoener Macro-Cyclization and Stereoselective Epoxidation Chemical & Pharmaceutical Bulletin. ,vol. 39, pp. 64- 74 ,(1991) , 10.1248/CPB.39.64
T. Schmittberger, D. Uguen, SODIUM SULPHIDE AS A MILD AND SELECTIVE DESILYLATING REAGENT Tetrahedron Letters. ,vol. 36, pp. 7445- 7448 ,(1995) , 10.1016/0040-4039(95)01549-3