3.2 Experimental Procedures
55
to room temperature, the mixture was diluted with EtOAc (730 μl), filtered
over a silica pad and was the residue was washed with EtOAc (2 × 360 μl).
The solution was concentrated under reduced pressure. Purification by
column chromatography (silica gel, heptane/EtOAc/AcOH = 55:40:5) gave
the target compound as colourless solid (34.6 μmol, 16.3 mg, 95 %). 20 %
overall yield starting from 5. The spectroscopic data is in accordance with
the literature.
[1,63]
1
H-NMR (600 MHz, CDCl 3 ): δ 5.31 (t, J = 3.7 Hz, 1 H, H
12 ), 3.65
(d, J = 11.3 Hz, 1 H, H
23a ), 3.42 (d, J = 11.4 Hz, 1 H, H
23b ), 2.83 (dd,
J = 13.9, 4.7 Hz, 1 H, H
18 ), 2.63 (ddd, J = 16.1, 13.3, 6.8 Hz, 1 H, H
2a ), 2.27
(ddd, J = 16.2, 5.3, 2.5 Hz, 1 H, H
2b ), 2.04–1.95 (m, 2 H, H
11a,16a ), 1.95–1.89
(m, 2 H, H
1a,11b ), 1.77 (td, J = 13.9, 4.5 Hz, 1 H, H
7a,22ab ), 1.74–1.67 (m, 2 H,
H
9,22a ), 1.66–1.54 (m, 4 H, H
5,7b,16b,19a ), 1.54–1.46 (m, 2 H, H
6a,15a ), 1.43–
1.32 (m, 4 H, H
1b,6b,15b,21a ), 1.27–1.20 (m, 1 H, H
21b ), 1.19–1.13 (m, 7 H,
H
19b,25,27 ), 1.13–1.08 (m, 1 H, H
22b ), 1.01 (s, 3 H, H
24 ), 0.93 (s, 3 H, H
30 ),
0.90 (s, 3 H, H
29 ), 0.83 (s, 3 H, H
26 ).
13 C-NMR (150 MHz, CDCl 3 ):
δ 219.3 (C
3 ), 182.1 (C
28 ), 143.9 (C
13 ), 122.4 (C
12 ), 67.0 (C
23 ), 52.5 (C
4 ),
49.3 (C
5 ), 46.9 (C
9 ), 46.6 (C
17 ), 45.9 (C
19 ), 41.9 (C
14 ), 41.2 (C
18 ), 39.4
(C
8 ), 38.9 (C
1 ), 36.8 (C
10 ), 35.3 (C
2 ), 33.9 (C
21 ), 33.2 (C
29 ), 32.5 (C
7 ),
32.2 (C
15 ), 30.8 (C
20 ), 27.8 (C
22 ), 26.0 (C
27 ), 23.7 (C
30 ), 23.6 (C
11 ), 23.1
(C
16 ), 19.2 (C
6 ), 17.3 (C
26 ), 17.0 (C
24 ), 15.3 (C
25 ). [α]
20
D
+70.9 (c 1.0,
CDCl 3 ). HRMS (ESI-TOF) m/z: [M + Na]
+ Calcd for C 30 H 45 BrNaO 4
+
493.3288; Found 493.3288.
55
to room temperature, the mixture was diluted with EtOAc (730 μl), filtered
over a silica pad and was the residue was washed with EtOAc (2 × 360 μl).
The solution was concentrated under reduced pressure. Purification by
column chromatography (silica gel, heptane/EtOAc/AcOH = 55:40:5) gave
the target compound as colourless solid (34.6 μmol, 16.3 mg, 95 %). 20 %
overall yield starting from 5. The spectroscopic data is in accordance with
the literature.
[1,63]
1
H-NMR (600 MHz, CDCl 3 ): δ 5.31 (t, J = 3.7 Hz, 1 H, H
12 ), 3.65
(d, J = 11.3 Hz, 1 H, H
23a ), 3.42 (d, J = 11.4 Hz, 1 H, H
23b ), 2.83 (dd,
J = 13.9, 4.7 Hz, 1 H, H
18 ), 2.63 (ddd, J = 16.1, 13.3, 6.8 Hz, 1 H, H
2a ), 2.27
(ddd, J = 16.2, 5.3, 2.5 Hz, 1 H, H
2b ), 2.04–1.95 (m, 2 H, H
11a,16a ), 1.95–1.89
(m, 2 H, H
1a,11b ), 1.77 (td, J = 13.9, 4.5 Hz, 1 H, H
7a,22ab ), 1.74–1.67 (m, 2 H,
H
9,22a ), 1.66–1.54 (m, 4 H, H
5,7b,16b,19a ), 1.54–1.46 (m, 2 H, H
6a,15a ), 1.43–
1.32 (m, 4 H, H
1b,6b,15b,21a ), 1.27–1.20 (m, 1 H, H
21b ), 1.19–1.13 (m, 7 H,
H
19b,25,27 ), 1.13–1.08 (m, 1 H, H
22b ), 1.01 (s, 3 H, H
24 ), 0.93 (s, 3 H, H
30 ),
0.90 (s, 3 H, H
29 ), 0.83 (s, 3 H, H
26 ).
13 C-NMR (150 MHz, CDCl 3 ):
δ 219.3 (C
3 ), 182.1 (C
28 ), 143.9 (C
13 ), 122.4 (C
12 ), 67.0 (C
23 ), 52.5 (C
4 ),
49.3 (C
5 ), 46.9 (C
9 ), 46.6 (C
17 ), 45.9 (C
19 ), 41.9 (C
14 ), 41.2 (C
18 ), 39.4
(C
8 ), 38.9 (C
1 ), 36.8 (C
10 ), 35.3 (C
2 ), 33.9 (C
21 ), 33.2 (C
29 ), 32.5 (C
7 ),
32.2 (C
15 ), 30.8 (C
20 ), 27.8 (C
22 ), 26.0 (C
27 ), 23.7 (C
30 ), 23.6 (C
11 ), 23.1
(C
16 ), 19.2 (C
6 ), 17.3 (C
26 ), 17.0 (C
24 ), 15.3 (C
25 ). [α]
20
D
+70.9 (c 1.0,
CDCl 3 ). HRMS (ESI-TOF) m/z: [M + Na]
+ Calcd for C 30 H 45 BrNaO 4
+
493.3288; Found 493.3288.