C[O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[H-].[Na+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][C:16]=1[C:27]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH:36]=O)[CH:31]=1)=[NH:28].C([O-])(O)=O.[Na+]>C1COCC1>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][C:16]=1[C:27]([NH:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:5][C:3]([OH:2])=[O:4])[CH:33]=[CH:34][CH:35]=1)=[NH:28]Trimethyl phosphonoacetate (176 mg, 0.97 mmol) in THF (1.5 mL) was added dropwise (caution—vigorous reaction!) to sodium hydride (60% in oil) (58 mg, 1.46 mmol) under an atmosphere of nitrogen at 0° C. The reaction mixture was stirred for 15 minutes at 0° C. and then aldehyde (57) (307 mg, 0.97 mmol) in THF (1.50 mL) was added. After 3-hours further sodium hydride (60% in oil) (1.5 eq) was added and the reaction mixture stirred at ambient temperature overnight. Saturated NaHCO3 solution was added and washed with EtOAc. The aqueous layer was acidified to pH 1 using 1.2 M HCl and extracted with EtOAc. The aqueous layer was then neutralised to pH 7 and extracted into EtOAc. The organic layers were combined, dried (MgSO4) and the solvent concentrated in vacuo. The residue was purified by Flash Master Jones Chromatography using a 2 g silica cartridge and a gradient of EtOAc in heptane and MeOH in EtOAc to yield the title compound. Yield: 25 mg, 7%; LC-MS tr 1.77 min; HPLC Purity: 91%; MS (ES+) m/z 361 (M+H); NMR (400 MHz; MeOH): δ 6.6 (d, 7.35-7.80 (m, 11H), 8.05 (m, 1H), 8.15 (d, 1H)
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