Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
(1S, 3R, 4R, 5R)-1-acetylferuloyl-3, 4-isopropylidene quinide, (55)
To a suspension of 3,4-isopropylidene-quinide (0.200 g, 0.934 mmol) and N,N-
(dimethylamino)pyridine (0.0057 g, 0.0467 mmol) in dichloromethane (10 ml)
was added pyridine (4 ml) followed by the addition of acetyl ferulic acid chloride
(0.261 g, 1.028 mmol). The reaction mixture was stirred for 15 hours at room
temperature and worked up by diluting with dichloromethane (50 ml), washing
with 2M HCl (10 ml), NaHCO 3 solution (10 ml) and brine (10 ml). The organic
layer was dried over MgSO 4 and the solvent was removed under reduced pressure
to give the title compound (55) as a white solid (0.350 g, 86.63%). Rf 0.50
[chloroform: acetone (8:2)]; ν max (KBr)/cm -1 : 1792, 1789, 1780 (C=O), 1658
(C Ar =C Ar ), 1464, 1469 (CH 3 ), 1028, 1013 (C-O); δ H (400 MHz, CDCl 3 ): 1.37 (3 H,
s, 9-H), 1.51 (3 H, s, 10-H), 2.15 (1 H, dd, J 12 and 2.4, 2-H ax ), 2.31 (1 H, m, 6-
H ax ), 2.32 (3 H, s, 22-H), 2.35 (1 H, m, 6-H eq ), 2.62 (1 H, d, J 12, 2-H eq ), 3.86 (1
H, s, 20-H), 4.20 (3 H, dd, J 16 and 6, 4-H), 4.43 (1 H, q, J 1.6, 3-H), 4.62 (1 H,
dd, J 9.2 and 3.2, 5-H), 6.37 (1 H, d, J 16, 12-H), 7.05 (1 H, d, J 7.6, 18-H), 7.12
(1 H, d, J 3.2, 15-H), 7.15 (1 H, dd, J 8.4 and 3.4, 19-H), 7.70 (1 H, d, J 16, 13-H);
δ C (125 MHz, CDCl 3 ): 20.93 (C-22), 24.81 (C-9), 27.94 (C-10), 39.63 (C-2),
39.84 (C-6), 56.51 (C-20), 71.10 (C-3), 71.43 (C-4), 72.15 (C-5), 74.82 (C-1),
109.36 (C-8), 112.36 (C-12), 120.05 (C-18), 121.87 (C-15), 123.77 (C-19), 133.45
(C-14), 141.25 (C-17), 143.87 (C-13), 151.75 (C-16), 168.05 (C-11), 169.02 (C-
21), 178.68 (C-7).
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