, 6R)-2-(acetoxymethyl)-6-(prop-2-yn-1-yloxy)tetrahydro-2H

, 00 g, 16.65 mmol) in acetic anhydride (20.46 mL, 216.47 mmol) was added sodium acetate (1.50 g, 18.32 mmol) under argon. The mixture was refluxed during 2 h and cooled to room temperature before being cooled in an ice bath. Water (50 mL) was added and the suspension was filtered

, CDCl 3 ): ? 1.42 (m, 9H, chromane CH 3 + linker CH 2 ), 1.91 (m, 3H, chromane 3-HaHb + triazole-CH 2 -CH 2 ), 1.98 (s, 3H, COCH 3 ), 2.00 (s, 3H, COCH 3 ), 2.03 (s, 3H, COCH 3 ), 2.09 (s, 6H, COCH 3 + chromane CH 3 ), 2.12 (m, 1H, chromane 3-HaHb), 2.14 (s, 3H, chromane CH 3 ), 2.19 (s, 3H, chromane CH 3 ), 2.59 (m, 2H, linker CH 2 ), 2.66 (m, 2H, chromane 4-H), 3.59 (d, J = 2.3 Hz, 2H, CH 2 CO), 3.74 (X part of an ABX system, ylidene)methyl)phenoxy)methyl)-2,5,7,8-tetramethylchroman-6-yl)hexyl)-1H-1,2,3-triazol-4-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (30) To a mixture of 28 (138 mg, 0.26 mmol) and 29 (100 mg, 0.26 mmol) were added t-BuOH (20 mL) and MeOH (2 mL) and sonication was applied. To the resulting solution was added a mixture of CuSO 4 (58 mg, 0.36 mmol) and sodium ascorbate (71 mg, 0.36 mmol) in water (0.5 mL), vol.1, pp.88-90

, 09 mL, 1.15 mg/mL) was added at room temperature and stirred under argon for 1 h. Amberlite ® IR 120H was added until neutral pH and the suspension was filtered to give after evaporation of the filtrate an orange liquid which was purified by reverse-phase column chromatography (eluent: H 2 O (0.1% TFA)/MeOH, 90:10 to 10:90) to afford after lyophilisation 71 mg (0.09 mmol, 100 % yield) of white powder, hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)hexyl)chroman-2-yl)methoxy)benzylidene)pyrrolidine-2,5-dione (31) A suspension of compound 30 (87 mg, 0.09 mmol) in anhydrous MeOH (5 mL) was sonicated until dissolution. A solution of MeONa in MeOH, vol.525, pp.126-128, 1043.

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