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Experimental Procedure for the One-Pot RCM and DDQ Oxidation.
Grubbs’ catalyst 6 (5 mol%) was added under argon atmosphere to a solution of 18 (62 mg, 0.2 mmol) in dry degassed CH2Cl2 (10 mL) and the resulting mixture was stirred at r.t. for 4 h. A solution of DDQ (91 mg, 0.4 mmol) in benzene (16 mL) was then added and the resulting mixture was heated to reflux for 16 h. Evaporation of the solvent in vacuo followed by chromatography of the residual mass on silica gel using 5% EtOAc-petroleum ether afforded 19 as a viscous liquid (30 mg, 54%). [α]D +6.5 (c 0.75, CH2Cl2). IR (neat): 2979, 1699, 1390, 1366 cm-1. 1H NMR (400 MHz, CDCl3, mixture of rotamers): δ = 7.31 (1 H, s), 6.27 (1 H, s), 6.04 (1 H, d, J = 4.1 Hz), 4.14 (1 H, d, J = 5.8 Hz), 4.03 (1 H, d, J = 4.2 Hz), 3.88-3.86 (2 H, m), 3.12 (1 H, d, J = 14.3 Hz), 3.01 (1 H, d, J = 14.3 Hz), 2.85-2.77 (2 H, m), 1.48 (s, 9 H), 1.24 (6 H, merged s). MS (TOF MS ES+): m/z = 304 [M+ + Na]. Anal. Calcd for C15H23NO4 (%): C, 64.0; H, 8.2; N, 5.0. Found: C, 64.3; H, 8.4; N, 4.8.
