[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14]NCC(O)CO)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].COC(C1N=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]([OH:45])[CH2:39]NC(C)(C)C)=[CH:32][CH:31]=2)NC=1)=O.[OH2:46]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][CH2:39][CH:38]([OH:45])[CH2:37][O:36][C:33]2[CH:34]=[CH:35][C:30]([CH:27]=[O:46])=[CH:31][CH:32]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]To a suspension of NaH (60% oil dispersion, 1.2 g., 0.03 mol.) in DMF (20 ml.) was added at 70° C. under N2 a solution 3 (37 g., 0.03 ml.) in DMF (30 ml.). After stirring for 15 minutes at 70° C. a solution of (S) 2 in DMF (50 ml.) was added dropwise. After the addition, the mixture was heated at 120° C. for 18 hours. The solution was then poured into H2O and extracted with EtOAc (3×). The organic extracts were washed with H2O (2×), saturated NaCl (1×), dried, filtered and concentrated to dryness. The residue was treated with H2O (250 ml.) and AcOH (25 ml.) and stirred overnight at room temperature. The solution was extracted with EtOAc (2×), neutralized with saturated Na2CO3 and extracted with CHCl3 (9×). The organic extracts were dried, filtered and concentrated to yield 8.5 g. of 4; 'H NMR (CDCl3) 2.7 (6H, m), 3.8 (6H, s), 4.1 (3H, m), 6.7 (3H, bs), 6.95 (2H, d), 7.75 (2H, d). ##STR116##
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