Reaction Steps
The procedure for 34 was used with alkyne 65 (1.69 g, 1.85 μmol) and Lindlar catalyst (ca. 200 mg) to yield 66 (1.70 g, quantitative) as a pale yellow oil: IR (CHCl3) 3477, 2955, 2856, 1471, 1448, 1386, 1254, 1057, 835, 773, 705 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.63-7.60 (m, 6H), 7.43-7.27 (m, 9H), 5.88-5.77 (m, 2H), 5.70 (t, J=10.1 Hz, 1H), 5.49 (dd, J=10.6, 8.4 Hz, 1H), 4.78 (m, 1H), 4.06 (m, 1H), 3.76-3.72 (m, 4H), 3.58 (t, J=3.6 Hz, 1H), 2.89 (m, 1H), 2.63 (m, 1H), 2.20 (d, J=2.8 Hz, 1H), 1.73-1.48 (m, 7H), 1.18 (d, J=6.9 Hz, 3H), 1.15 (d, J=7.0 Hz, 3H), 1.08-1.02 (m, 27H), 0.29-0.20 (m, 18H); 13C NMR (75 MHz, CDCl3) δ 144.3, 134.9, 134.4, 131.5, 128.6, 127.7, 127.0, 126.8, 86.7, 79.8, 72.8, 65.0, 64.7, 63.5, 42.1, 39.7, 37.9, 35.9, 31.4, 29.9, 26.2, 26.0, 25.9, 20.1, 18.4, 18.3, 18.0, 14.9, 14.5, −3.6, −3.8, −4.5, −4.6, −5.3; LRMS (ESI) 937.5 [M+Na]+; HRMS (ESI) calcd for C55H90O5Si3Na 937.5994 [M+Na]+, found 937.6016; [α]20D+2.1 (c 0.92, CHCl3).
