[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:24])[C@H:15]([CH2:16][S:17]2=[O:20])[C@:14]2([CH3:21])[C@H:9]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[CH:4][C:3]=1[C:25]([OH:27])=O.[CH3:28][N:29](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN>C1COCC1.CN(C=O)C.CCOC(C)=O>[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:24])[C@H:15]([CH2:16][S:17]2=[O:20])[C@:14]2([CH3:21])[C@H:9]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[CH:4][C:3]=1[C:25]([NH:29][CH3:28])=[O:27]A mixture of (1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8-oxo-8λ4-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4-carboxylic acid (71) (0.40 g, 1.1 mmol), HATU (0.49 g, 1.3 mmol), Hunig's base (0.24 mL, 1.4 mmol), methylamine (2 M in diethyl ether, 2.7 mL, 5.4 mmol) in anhydrous THF (10 mL) and DMF (2 mL) was placed in a sealed vessel. The reaction was stirred at room temperature for 18 h. The reaction was diluted with EtOAc and washed with water and brine. The organic layer was separated and concentrated to dryness. The crude product was purified by flash chromatography on silica gel (CH2Cl2/EtOAc, 7:3) to yield (1R,10R,11S,16S)-5-hydroxy-N,1,11,15,15-pentamethyl-8-oxo-8λ4-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4-carboxamide (72) (0.07 g, 16% yield) as a white solid.
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