Chemistry & Biodiversity
10.1002/cbdv.201800560
Chem. Biodiversity
Hz, 1H), 4.13 – 4.05 (m, 2H), 3.97 (s, 3H), 3.36 (d, J = 6.5 Hz, 1H), 2.29 (p, J = 6.9 Hz, 1H), 2.25 (d, J = 11.0 Hz, 1H), 2.19 (dt, J = 19.4, 9.4 Hz, 1H), 2.10
(s, 1H), 2.06 (dd, J = 16.1, 8.6 Hz, 1H), 1.76 (dd, J = 14.5, 2.9 Hz, 1H), 1.69 – 1.62 (m, 2H), 1.60 (s, 1H), 1.46 (ddd, J = 13.0, 9.7, 2.7 Hz, 1H), 1.42 (s, 3H),
13
1
3
.39 – 1.36 (m, 1H), 1.34 (s, 1H), 1.17 (s, 3H), 1.13 (td, J = 14.2, 4.4 Hz, 1H), 0.88 (d, J = 7.0 Hz, 3H), 0.71 (d, J = 7.0 Hz, 3H). C NMR (151 MHz, CDCl )
δ 216.77, 166.09, 152.84, 138.66, 117.35, 74.58, 71.03, 58.03, 45.41, 44.53, 44.00, 41.85, 36.61, 36.01, 35.88, 34.42, 33.58, 30.36, 26.82, 26.47, 24.81, 16.71,
+
1
4.75, 11.46 . HRMS (ESI): calcd for C24H36N4O4SNa [M + Na] : 499.2305; found, 499.2363.
4
-O-((( 1-methyltetrazole-5-yl)sulfinyl)acetyl)mutilin(4g)
1
Yield: 11%. H NMR (600 MHz, CDCl
3
) δ 6.41 – 6.29 (m, 1H), 5.79 (dd, J = 8.5, 5.3 Hz, 1H), 5.34 – 5.25 (m, 1H), 5.20 (dd, J = 16.8, 5.2 Hz, 1H), 4.49 (d, J
=
17.3 Hz, 1H), 4.34 (d, J = 15.5 Hz, 3H), 4.23 (dd, J = 44.6, 15.5 Hz, 1H), 3.40 – 3.32 (m, 1H), 2.30 – 2.22 (m, 2H), 2.22 – 2.17 (m, 1H), 2.14 – 2.03 (m,
2
H), 1.80 – 1.74 (m, 1H), 1.71 – 1.61 (m, 3H), 1.47 (d, J = 5.6 Hz, 3H), 1.41 – 1.36 (m, 3H), 1.28 (dd, J = 16.5, 9.9 Hz, 1H), 1.17 (d, J = 9.7 Hz, 3H), 1.12
13
(
dd, J = 13.8, 4.1 Hz, 1H), 0.88 (d, J = 7.0 Hz, 3H), 0.74 – 0.71 (m, 3H). C NMR (151 MHz, CDCl
3
) δ 216.54, 216.51, 163.07, 162.05, 154.89, 154.77,
1
3
38.67, 138.40, 117.61, 117.39, 74.53, 71.80, 71.75, 58.45, 58.38, 57.92, 57.90, 45.38, 44.64, 44.10, 44.05, 41.82, 41.80, 36.55, 36.54, 36.01, 35.48, 35.45,
+
4.38, 30.30, 26.81, 26.49, 26.42, 24.79, 16.81, 14.79, 14.68, 11.47, 11.46 . HRMS (ESI): calcd for C24H36N4O5SNa [M + Na] : 515.2304; found, 515.2296.
4
-O-(((1-[2-(Dimethylamino)ethyl]-1H-tetrazole -5-yl)sulfanyl)acetyl)mutilin(4H)
1
Yield: 53 %. H NMR (600 MHz, CDCl
3
) δ 6.37 (dd, J = 17.4, 11.0 Hz, 1H), 5.73 (d, J = 8.5 Hz, 1H), 5.29 (dd, J = 11.0, 1.2 Hz, 1H), 5.18 (dd, J = 17.4, 1.3
Hz, 1H), 4.42 (t, J = 5.8 Hz, 2H), 4.14 – 3.99 (m, 2H), 3.35 (s, 1H), 2.87 (s, 2H), 2.35 (s, 6H), 2.30 – 2.27 (m, 1H), 2.25 (d, J = 11.1 Hz, 1H), 2.15 – 2.19 (m,
H), 2.09 (s, 1H), 2.05 (dd, J = 16.1, 8.6 Hz, 1H), 1.76 (dd, J = 14.5, 2.9 Hz, 1H), 1.69 – 1.61 (m, 2H), 1.45 (ddd, J = 13.0, 9.6, 2.5 Hz, 2H), 1.42 (s, 3H), 1.37
1
13
(
dd, J = 14.3, 3.2 Hz, 1H), 1.31 (d, J = 16.1 Hz, 1H), 1.17 (s, 3H), 1.12 (td, J = 14.2, 4.4 Hz, 1H), 0.87 (d, J = 7.1 Hz, 3H), 0.70 (d, J = 7.1 Hz, 3H). C NMR
3
(151 MHz, CDCl ) δ 216.78, 166.33, 153.28, 138.68, 117.36, 74.60, 70.86, 58.05, 57.51, 45.42, 45.21, 44.56, 44.00, 41.86, 36.63, 36.22, 36.01, 34.43, 30.37,
+
2
4
9.70, 26.83, 26.44, 24.82, 16.73, 14.77, 11.47 . HRMS (ESI): calcd for C27H43N5O4SNa [M + Na] : 556.2933; found, 556.2920.
-O-(((1-[2-(Dimethylamino)ethyl]-1H-tetrazole-5-yl)sulfinyl)acetyl)mutilin(4h)
1
Yield: 16%. H NMR (600 MHz, CDCl
3
) δ 6.42 – 6.32 (m, 1H), 5.77 – 5.68 (m, 1H), 5.29 (dq, J = 16.0, 9.9, 8.1 Hz, 1H), 5.18 (dt, J = 16.2, 7.9 Hz, 1H), 4.40
(t, J = 6.2 Hz, 1H), 4.17 – 3.97 (m, 2H), 3.49 (s, 1H), 3.35 (d, J = 6.2 Hz, 1H), 3.12 (q, J = 7.3 Hz, 1H), 2.84 (t, J = 6.1 Hz, 1H), 2.81 – 2.61 (m, 2H), 2.38 –
2
.14 (m, 6H), 2.06 (dd, J = 26.6, 14.7 Hz, 2H), 1.76 (d, J = 14.4 Hz, 1H), 1.65 (q, J = 11.8, 10.7 Hz, 2H), 1.46 (d, J = 11.8 Hz, 1H), 1.42 (s, 3H), 1.39 – 1.24
13
(
m, 4H), 1.17 (s, 3H), 1.11 (d, J = 14.7 Hz, 1H), 0.99 – 0.91 (m, 1H), 0.87 (d, J = 6.8 Hz, 3H), 0.75 – 0.66 (m, 3H). C NMR (151 MHz, CDCl
3
) δ 216.85,
1
1
66.34, 138.71, 117.32, 74.59, 70.87, 58.06, 57.53, 45.54, 45.42, 45.24, 44.56, 44.00, 41.86, 36.63, 36.22, 36.01, 35.75, 34.43, 30.37, 26.82, 26.48, 24.82,
+
6.72, 14.77, 11.47 . HRMS (ESI): calcd for C27H43N5O5SNa [M + Na] : 572.2883; found, 572.2883.
4
-O-(((Benzothiazole-2-yl)sulfanyl)acetyl)mutilin(5A)
1
Yield: 80%. H NMR (600 MHz, CDCl
3
) δ 7.80 (d, J = 8.2 Hz, 1H), 7.74 (d, J = 12.0, 1H), 7.40 (t, J = 7.4 Hz, 1H), 7.29 (t, J = 7.6 Hz, 1H), 6.42 (dd, J = 17.4,
1
1
1.0 Hz, 1H), 5.77 (d, J = 8.6 Hz, 1H), 5.26 (d, J = 11.7 Hz, 1H), 5.12 (d, J = 16.6 Hz, 1H), 4.15 – 4.10 (m, 1H), 4.03 (d, J = 16.3 Hz, 1H), 3.32 (d, J = 6.4 Hz,
H), 2.32 – 2.28 (m, 1H), 2.24 – 2.16 (m, 2H), 2.05 (d, J = 15.3 Hz, 2H), 1.99 (dd, J = 16.0, 8.6 Hz, 1H), 1.74 (d, J = 14.5 Hz, 1H), 1.63 (dd, J = 22.2, 11.2
Hz, 3H), 1.43 (s, 3H), 1.35 (d, J = 14.0 Hz, 1H), 1.32 – 1.24 (m, 2H), 1.12 (dd, J = 14.2, 4.4 Hz, 1H), 1.07 (s, 3H), 0.85 (d, J = 7.0 Hz, 3H), 0.77 (d, J = 7.2
13
Hz, 3H). C NMR (151 MHz, CDCl
3
) δ 216.93, 166.82, 164.61, 152.67, 138.77, 135.45, 126.04, 124.49, 121.67, 121.06, 117.20, 74.58, 70.23, 58.11, 45.42,
+
4
5
4.43, 43.91, 41.87, 36.75, 35.99, 35.71, 34.44, 30.41, 26.85, 26.32, 24.82, 16.80, 14.83, 11.45 . HRMS (ESI): calcd for C29H37NO4S2Na [M + Na] :
50.2062; found, 550.2075.
4
-O-((( Benzothiazole-2-yl)sulfinyl)acetyl)mutilin(5a)
1
Yield: 77%. H NMR (600 MHz, CDCl
3
) δ 8.06 (dd, J = 8.2, 3.6 Hz, 2H), 8.01 (dd, J = 8.0, 2.2 Hz, 2H), 7.60 – 7.56 (m, 2H), 7.53 – 7.49 (m, 2H), 6.45 – 6.38
(m, 2H), 5.83 (dd, J = 19.0, 8.6 Hz, 2H), 5.35 – 5.29 (m, 3H), 5.21 (dd, J = 17.4, 1.3 Hz, 2H), 4.20 – 4.17 (m, 1H), 4.16 (s, 1H), 4.13 – 4.08 (m, 1H), 3.99 (d,
J = 14.9 Hz, 1H), 3.35 (dd, J = 12.3, 6.5 Hz, 2H), 2.92 (d, J = 45.1 Hz, 0H), 2.31 – 2.16 (m, 6H), 1.95 – 2.05 (m, 5H), 1.79 – 1.74 (m, 2H), 1.68 – 1.61 (m,
5
1
2
7
H), 1.48 (s, 3H), 1.45 (dd, J = 8.0, 4.6 Hz, 2H), 1.43 (s, 1H), 1.38 (td, J = 9.9, 9.4, 5.5 Hz, 2H), 1.31 (s, 3H), 1.27 – 1.24 (m, 1H), 1.15 (d, J = 5.0 Hz, 6H),
13
3
.11 (ddd, J = 14.4, 10.4, 4.2 Hz, 2H), 0.88 (d, J = 7.0 Hz, 6H), 0.78 (d, J = 7.2 Hz, 3H), 0.73 (d, J = 7.2 Hz, 3H). C NMR (151 MHz, CDCl ) δ 216.72,
16.70, 175.87, 175.87, 163.30, 163.00, 153.64, 153.62, 138.72, 138.67, 127.13, 127.11, 126.50, 126.47, 124.11, 124.10, 122.32, 122.27, 117.43, 117.39,
4.56, 71.23, 71.20, 60.85, 60.64, 58.05, 57.95, 45.41, 45.39, 44.70, 44.53, 44.05, 41.85, 41.82, 36.68, 36.60, 36.06, 36.03, 34.41, 30.36, 30.33, 26.82, 26.81,
12
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