Fig. 4

Library of 242 DOS compounds synthesized to study antibacterial activity [20]. Reagents and conditions: a LiBr, 1,8-diazabicyclo[5.4.0]undec-7-ene, R1 CHO, MeCN; b (R)-QUINAP, AgOAc, iPr2NEt, THF, 788C!258C; c AD-mix, (DHQD)PHAL, THF/H2O (1:1); d chiral bis(oxazoline), Cu(OTf)2, 3 E M.S., CH2Cl2, C5H6; e R2 COCl, DMAP, pyridine, CH2Cl2; f R3 CHO, BH3·pyridine, MeOH; g SOCl2, pyridine, CH2Cl2, 40 8C; h R4 Br, Ag2O, CH2Cl2, 40 8C; i R5 C(O)R5, TsOH, DMF, 658C; j R6 CHO, TsOH, DMF, 65 8C; k NaN3, DMF, 1008C then dimethyl acetylenedicarboxylate, PhMe, 658C; l mCPBA, CH2Cl2 then MeOH, 658C; m CH2=CHCO2Bn, PhMe, 1208C, Grubbs II, CH2=CH2; n OsO4, NMO, CH3C(O)CH3/ H2O (10:1); o RNH2, Me2AlCl, PhMe 1208C; then NaH, R11X, DMF, THF; then PhMe, 1208C, Grubbs II, CH2=CH2; p NaIO4, THF/H2O (1:1); then R7 NH2, NaB(OAc)3H, CH2Cl2; q NaIO4, THF/H2O (1:1); then R8 NHR8, NaB(OAc)3H, CH2Cl2; r R9 CHO, DMF, TsOH, 60 8C; s R10C(O)R10, DMF, TsOH, 608C. DMF = N,N-dimethylformamide, THF = tetrahydrofuran, DMAP = N,N-dimethylaminopyridine, (DHQD)PHAL = hydroquinidine 1,4-phthalazinediyl diether, mCPBA = meta-chloroperbenzoic acid, Ts = para-toluenesulfonyl, Grubbs II = 1,3-(bis-(mesityl)-2-imidazolidinyl-idene) dichloro (phenylmethylene) (tricyclohexylphosphine) ruthenium, NMO = 4-methylmorpholine-N-oxide, OTf = CF3SO3, Bn = benzyl, QUINAP = 1-(2-diphenylphosphino-1-naphthyl)isoquinoline