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Mec C02CH2Ph Me d CHO Me f COCF3 Et 0 s 0 2 h Me QCOCF3 BU hCOCF3 BU '+AOR DNPHN R3 OH H DNP Paper 4/0 1 768D

Shorter and more efficient routes to 6′‐des(N‐methyl)sannamycin A (1) and its 2′‐epi analog 2 have been elaborated with the proven sannamine‐type acceptor 10 and the glycosyl donors 5–8 featuring novel protecting patterns. With glycal 9 as glycosyl donor (and 10) an expedient access to 2′‐desamino‐ (3) and 2′‐desamino‐2′‐epi‐hydroxysannamycin A (4) has been opened. For 4 a modest antibacterial activity was found, while 3 was inactive.

Total Syntheses of Enantiomerically Pure D-and L-Glycosyl Donors as Components of Sannamycin-Type Aminoglycoside Antibiotics.-Both enantiomers of the compounds (XV) to (XVIII), which are suitable in this form as glycosyl donors, are prepared from racemic acrolein dimer (I) using methods similar to that described for (XV). The products are obtained as anomeric mixtures. -(LUDIN, C.; SCHWESINGER, B.; SCHWESINGER, R.; MEIER, W.; SEITZ, B.; WELLER, T.; HOENKE, C.; HAITZ, S.; ER-BECK, S.; PRINZBACH, H.; J. Chem. Soc., Perkin Trans. I (1994) 19, 2685-2701; Inst. Org. Chem. Biochem., Univ. Freiburg, D-79104 Freiburg/Br., Germany; EN)

Sannamycin-Type Aminoglycoside Antibiotics -Efficient Syntheses -Biological Activity.-Efficient syntheses of title compounds (IV) are developed based on glycosylations of the proven sannamycin-type acceptor (I) with glycosyl donors featuring novel protection patterns. Compounds (IVc,d) are screened for antibacterial activity. (IVd) exhibits modest activity, while (IVc) is found to be inactive. -(ERBECK, S.; LIANG, X.; HUNKLER, D.; KRIEGER, R.; PRINZBACH, H.; Eur.