C[O:2]/[CH:3]=[CH:4]/[C:5]([CH3:14])([CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].C(O)=O.OC1C2NC(=O)SC=2C([C@@H](O)CNCCC(C)(C)CCCCCCN2CCC3(OCCN(C(C4N=C(C(C)C)SC=4)=O)C3)CC2)=CC=1.C(N(CC)CC)C.[CH3:72][S:73](Cl)(=[O:75])=[O:74]>ClCCl>[CH3:72][S:73]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([CH3:14])([CH3:13])[CH2:4][CH:3]=[O:2])(=[O:75])=[O:74]A mixture of (E)-9-methoxy-7,7-dimethylnon-8-en-1-ol and (Z)-9-methoxy-7,7-dimethylnon-8-en-1-ol (example 279, step d) (1.6 g) was dissolved in dichloromethane (15 mL) and triethylamine (1.33 mL) was added then the mixture was cooled to 0° C. in an ice bath under argon. Methanesulfonyl chloride (0.68 mL) was added dropwise over 5 minutes and the reaction mixture was stirred at 0° C. for 15 minutes and then at room temperature for 1 hour. The reaction mixture was washed with brine (2×30 mL), dried over magnesium sulfate, filtered and evaporated under vacuum to give the crude product. Purification was by silica gel chromatography, eluting with 0-100% ethyl acetate in cyclohexane to afford the subtitled compound as a colourless oil. Yield 1.2 g.
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