10.1002/adsc.201900564
Advanced Synthesis & Catalysis
Tyrosine (3b). The Product was obtained as a yellow oil.
Tyrosine (3g). The Product was obtained as a yellow oil.
Yield: 118 mg (84%). [α]D20 (c = 0.2, CHCl3): + 20.6 º. IR
(film) cm−1: 3250, 2879, 1687, 1654, 1611, 1568, 1460,
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Yield: 56 mg (53%). [α]D (c = 0.2, CHCl3): + 35.0 º. IR
(film) cm−1: 3227, 2879, 1654, 1609, 1555, 1456, 1402,
1
1
1322, 1238, 1171, 1123, 1104, 981, 814, 747, 711, 674. H
1434, 1322, 1229, 1188, 1128, 1009, 979, 802. H NMR
NMR (300 MHz, CDCl3) δ 10.06 (d, J = 7.7 Hz, 1H), 7.62
– 7.54 (m, 2H), 7.43 – 7.31 (m, 3H), 7.02 (d, J = 8.5 Hz,
2H), 6.91 (d, J = 8.5 Hz, 2H), 6.24 (d, J = 7.7 Hz, 1H), 4.97
(d, J = 4.1 Hz, 1H), 4.57 – 4.45 (m, 1H), 3.64 (s, 3H), 2.98
(ddt, J = 19.6, 13.8, 6.0 Hz, 2H), 1.39 (s, 9H). 13C NMR (75
MHz, CDCl3) δ 190.6, 172.2, 167.1, 156.3, 155.0, 132.8,
(300 MHz, CDCl3) δ 10.01 (d, J = 7.7 Hz, 1H), 7.62 (s, 1H),
7.46 (d, J = 8.0 Hz, 2H), 7.17 (d, J = 7.9 Hz, 2H), 6.91 (d, J
= 8.1 Hz, 1H), 6.60 (d, J = 8.3 Hz, 1H), 6.24 (d, J = 7.7 Hz,
1H), 5.13 – 5.02 (m, 1H), 4.54 – 4.43 (m, 1H), 3.67 (s, 3H),
2.95 (ddd, J = 39.0, 13.3, 6.4 Hz, 2H), 2.34 (s, 3H), 1.40 (s,
9H). 13C NMR (75 MHz, CDCl3) δ 190.4, 171.9, 167.1,
131.4, 131.1, 130.8, 130.0, 128.9, 128.6, 127.5, 121.3, 116.9, 155.3, 154.9, 142.4, 140.6, 133.2, 130.5, 129.9, 129.2, 127.3,
116.5, 80.0, 54.4, 52.1, 37.7, 28.3. HRMS (ESI-TOF) m/z,
116.0, 116.0, 85.7, 80.0, 54.3, 52.2, 37.1, 28.3, 21.5.
HRMS (ESI-TOF) m/z, calcd for [C25H28INO6 + H]+:
566.1040, found: 566,1037.
calcd for [C24H27NO6 + H]+: 426.1917, found: 426.1915.
Tyrosine (3c). The Product was obtained as a yellow foam.
Yield: 136 mg (87%). MP 79-91 °C. [α]D20 (c = 0.2, CHCl3):
+ 28.5 º. IR (solid) cm−1: 3233, 2879, 1687, 1657, 1566,
1553, 1434, 1322, 1259,1188, 1128, 1011, 976, 821, 737,
Tyrosine (3h). The Product was obtained as a yellow oil.
20
Yield: 54 mg (49%). [α]D (c = 0.2, CHCl3): + 22.4 º. IR
(film) cm−1: 3259, 2879, 2758, 1687, 1654, 1603, 1553,
1456, 1322, 1236, 1171, 1125, 1106, 1022, 979, 799, 713.
1H NMR (300 MHz, CDCl3) δ 10.03 (d, J = 7.7 Hz, 1H),
7.47 (d, J = 6.5 Hz, 2H), 7.16 (d, J = 6.8 Hz, 2H), 7.03 (d, J
= 6.7 Hz, 2H), 6.90 (d, J = 6.6 Hz, 2H), 6.22 (d, J = 7.7 Hz,
1H), 4.98 (d, J = 3.5 Hz, 1H), 4.59 – 4.44 (m, 1H), 3.65 (s,
3H), 2.99 (tt, J = 17.0, 9.7 Hz, 2H), 2.34 (s, 3H), 1.39 (s,
1
678. H NMR (300 MHz, CDCl3) δ 10.03 (d, J = 7.7 Hz,
1H), 7.68 – 7.59 (m, 5H), 7.59 – 7.51 (m, 2H), 7.40 (dt, J =
13.2, 6.9 Hz, 3H), 6.93 (d, J = 8.3 Hz, 1H), 6.65 (d, J = 8.3
Hz, 1H), 6.32 (d, J = 7.6 Hz, 1H), 5.07 (d, J = 6.8 Hz, 1H),
4.54 – 4.43 (m, 1H), 3.65 (s, 3H), 2.95 (ddd, J = 39.5, 13.7,
5.8 Hz, 2H), 1.39 (s, 9H). 13C NMR (75 MHz, CDCl3) δ
190.4, 171.9, 166.6, 155.3, 154.9, 144.4, 140.7, 139.5, 133.3, 9H). 13C NMR (75 MHz, CDCl3) δ 190.7, 172.2, 167.3,
130.9, 130.6, 129.0, 128.2, 127.9, 127.7, 127.0, 116.5, 116.0, 156.4, 155.0, 142.1, 130.9, 130.7, 129.9, 129.7, 127.4, 116.8,
85.8, 80.1, 54.3, 52.3, 37.1, 28.3. HRMS (ESI-TOF) m/z,
115.9, 80.0, 54.4, 52.1, 37.7, 28.2, 21.5. HRMS (ESI-TOF)
m/z, calcd for [C25H29NO6 + H]+: 440.2073, found:
440.2068.
calcd for [C30H30INO6 + H]+: 628.1196, found: 628.1192.
Tyrosine (3d). The Product was obtained as a yellow crystal.
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Yield: 105 mg (84%). MP 149-151 °C. [α]D (c = 0.2,
Tyrosine (3i). The Product was obtained as a yellow oil.
CHCl3): + 26.0 º. IR (solid) cm−1: 3289, 2887, 1700, 1639,
Yield: 48 mg (33%). [α]D (c = 0.2, CHCl3): + 32.9 º. IR
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1613, 1551, 1458, 1398, 1363, 1303, 1214, 1168, 1119,
(film) cm−1: 3242, 2879, 2836, 1685, 1648, 1566, 1432,
1391, 1322, 1184, 1121, 1024, 1007, 985, 814, 713, 680. 1H
NMR (300 MHz, CDCl3) δ 10.02 (d, J = 7.8 Hz, 1H), 9.63
(d, J = 7.5 Hz, 1H), 7.64 (s, 1H), 7.30 (dq, J = 16.7, 7.5 Hz,
4H), 7.14 (ddd, J = 15.7, 8.2, 5.2 Hz, 2H), 6.86 (dd, J = 8.2,
4.1 Hz, 1H), 5.57 (d, J = 7.8 Hz, 1H), 5.07 (d, J = 5.7 Hz,
1H), 4.97 (d, J = 7.5 Hz, 1H), 4.61 – 4.47 (m, 1H), 3.72 (d,
J = 8.2 Hz, 3H), 3.22 – 3.05 (m, 4H), 3.05 – 2.89 (m, 1H),
1
1095, 1022, 994, 974, 819, 789, 741, 715, 668. H NMR
(300 MHz, CDCl3) δ 10.07 (d, J = 7.7 Hz, 1H), 7.65 (d, J =
8.2 Hz, 3H), 7.62 – 7.52 (m, 4H), 7.41 (dt, J = 13.4, 7.1 Hz,
3H), 7.05 (d, J = 8.5 Hz, 2H), 6.94 (d, J = 8.5 Hz, 2H), 6.30
(d, J = 7.7 Hz, 1H), 5.03 – 4.92 (m, 1H), 4.60 – 4.44 (m,
1H), 3.64 (s, 3H), 2.98 (ddt, J = 19.6, 14.0, 6.1 Hz, 2H), 1.38
(s, 9H). 13C NMR (75 MHz, CDCl3) δ 190.6, 172.2, 166.8,
156.5, 144.2, 139.6, 131.5, 131.1, 130.8, 128.9, 128.2, 127.9, 2.84 (t, J = 7.8 Hz, 1H), 2.54 – 2.45 (m, 1H), 1.43 (d, J =
127.6, 127.0, 116.8, 116.4, 80.0, 54.4, 52.2, 37.7, 28.3.
HRMS (ESI-TOF) m/z, calcd for [C30H31NO6 + H]+:
502.2230, found: 502.2226.
5.9 Hz, 9H). 13C NMR (75 MHz, CDCl3) δ 190.2, 189.4,
176.7, 171.8, 155.0, 153.2, 151.5, 140.9, 139.9, 139.5, 136.5,
135.0, 130.9, 130.7, 128.7, 128.6, 128.6, 128.5, 128.3, 126.7,
126.6, 122.3, 119.2, 115.1, 108.4, 89.8, 88.5, 80.2, 52.4,
37.6, 34.6, 33.8, 32.8, 32.7, 28.3. HRMS (ESI-TOF) m/z,
calcd for [C26H30INO6 + H]+: 580.1196, found: 580.1193.
Tyrosine (3e). The Product was obtained as a yellow oil.
Yield: 110 mg (71%). [α]D20 (c = 0.2, CHCl3): + 31.7 º. IR
(film) cm−1: 3252, 2857, 2833, 2762, 1685, 1654, 1611,
1601, 1566, 1555, 1432, 1322, 1229, 1184, 1123, 1009, 978,
Tyrosine (3j). The Product was obtained as a yellow foam.
Yield: 150 mg (95%). MP 85-87 °C. [α]D20 (c = 0.2, CHCl3):
+ 31.0 º. IR (solid) cm−1: 3229, 2875, 2753, 1685, 1654,
1601, 1560, 1430, 1346, 1322, 1300, 1229, 1179, 1158,
1127, 1086, 1054, 987, 901, 827, 789. 1H NMR (300 MHz,
CDCl3) δ 9.62 (d, J = 7.6 Hz, 1H), 8.15 (s, 1H), 8.02 (s, 1H),
7.84 (s, 1H), 7.76 – 7.61 (m, 3H), 7.55 (d, J = 8.7 Hz, 1H),
7.27 – 7.04 (m, 4H), 6.88 (d, J = 8.4 Hz, 1H), 6.65 (d, J =
8.3 Hz, 1H), 6.37 (d, J = 7.6 Hz, 1H), 5.35 (d, J = 7.7 Hz,
1
814. H NMR (300 MHz, CDCl3) δ 10.00 (d, J = 7.7 Hz,
1H), 7.62 (s, 1H), 7.48 (d, J = 8.1 Hz, 2H), 7.18 (d, J = 8.1
Hz, 2H), 6.91 (d, J = 7.3 Hz, 1H), 6.61 (d, J = 8.3 Hz, 1H),
6.26 (d, J = 7.7 Hz, 1H), 5.06 (d, J = 6.6 Hz, 1H), 4.54 –
4.42 (m, 1H), 3.66 (s, 3H), 2.95 (ddd, J = 36.6, 13.7, 5.5 Hz,
2H), 2.59 (t, J = 7.7 Hz, 2H), 1.58 (p, J = 7.3 Hz, 2H), 1.40
(s, 9H), 1.34 – 1.25 (m, 4H), 0.87 (t, J = 6.6 Hz, 3H). 13C
NMR (75 MHz, CDCl3) δ 190.5, 171.9, 167.1, 155.4, 154.9,
147.4, 140.6, 133.1, 130.5, 129.4, 129.2, 127.3, 116.0, 115.8, 1H), 5.20 (d, J = 8.1 Hz, 1H), 5.08 (d, J = 8.4 Hz, 1H), 4.47
85.7, 80.1, 54.3, 52.2, 37.1, 35.8, 31.4, 30.6, 28.3, 22.4, 13.9. (s, 1H), 3.94 (s, 1H), 3.89 (s, 3H), 3.73 (s, 1H), 3.61 (s, 3H),
HRMS (ESI-TOF) m/z, calcd for [C29H36INO6 + H]+:
3.20 – 2.76 (m, 3H), 1.44 (s, 4H), 1.37 (s, 9H). 13C NMR
(75 MHz, CDCl3) δ 192.3, 190.4, 175.3, 171.9, 171.9, 167.2,
159.5, 159.4, 155.6, 154.9, 152.1, 141.0, 140.7, 136.6, 136.3,
136.2, 133.2, 131.0, 130.6, 130.3, 128.3, 128.1, 127.8, 127.8,
127.2, 127.0, 126.9, 126.7, 124.0, 122.4, 120.0, 119.9, 116.2,
115.9, 109.4, 105.8, 105.8, 89.8, 85.7, 80.0, 55.4, 54.3, 52.4,
52.2, 37.3, 37.0, 28.3, 28.2. HRMS (ESI-TOF) m/z, calcd
for [C29H30INO7 + H]+: 632.1145, found: 632.1143.
622.1666, found: 622.1661.
Tyrosine (3f). The Product was obtained as a yellow oil.
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Yield: 58 mg (47%). [α]D (c = 0.2, CHCl3): + 34.5 º. IR
(film) cm−1: 3250, 2857, 2833, 2762, 1687, 1655, 1611,
1553, 1454, 1322, 1240, 1173, 1127, 1106, 1022, 979, 810.
1H NMR (300 MHz, CDCl3) δ 10.03 (d, J = 6.0 Hz, 1H),
7.49 (d, J = 6.5 Hz, 2H), 7.16 (d, J = 6.6 Hz, 2H), 7.03 (d, J
= 6.9 Hz, 2H), 6.91 (d, J = 6.7 Hz, 2H), 6.24 (d, J = 6.0 Hz,
1H), 5.00 (d, J = 8.5 Hz, 1H), 4.52 (d, J = 7.3 Hz, 1H), 3.64
(s, 3H), 2.98 (qd, J = 14.3, 6.0 Hz, 2H), 2.58 (t, J = 7.8 Hz,
2H), 1.59 (p, J = 7.6, 6.8 Hz, 2H), 1.39 (s, 9H), 1.35 – 1.21
(m, 4H), 0.88 (t, J = 6.1 Hz, 3H). 13C NMR (75 MHz,
CDCl3) δ 190.7, 172.2, 167.3, 156.6, 155.0, 147.1, 131.0,
130.9, 130.7, 130.0, 129.0, 128.6, 127.4, 116.8, 115.9, 80.0,
54.4, 52.1, 37.7, 35.8, 31.4, 30.7, 28.3, 22.4, 13.9. HRMS
(ESI-TOF) m/z, calcd for [C29H37NO6 + H]+: 496.2699,
found: 496.2695.
Tyrosine (3k). The Product was obtained as a yellow foam.
Yield: 126 mg (88%). MP 65-68 °C. [α]D20 (c = 0.2, CHCl3):
+ 33.0 º. IR (solid) cm−1: 3170, 2877, 1685, 1648, 1601,
1566, 1432, 1322, 1257, 1227, 1184, 1125, 1102, 1009, 978,
817. 1H NMR (300 MHz, CDCl3) δ 10.01 (s, 1H), 7.63 (s,
1H), 7.53 (d, J = 8.1 Hz, 2H), 7.47 (d, J = 8.1 Hz, 2H), 6.93
(d, J = 8.5 Hz, 1H), 6.59 (d, J = 8.4 Hz, 1H), 6.27 (d, J = 7.5
Hz, 1H), 5.07 (d, J = 8.2 Hz, 1H), 4.49 (d, J = 7.4 Hz, 1H),
3.67 (s, 3H), 3.22 (s, 1H), 2.95 (ddd, J = 42.6, 14.2, 6.3 Hz,
2H), 1.40 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 191.5,
190.2, 173.9, 171.9, 171.8, 165.8, 155.0, 154.9, 151.8, 141.0,
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