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(500 MHz, CDCl3): δ = 7.87 (dd, J = 7.6, 1.6 Hz, 1 H), 7.55 (m, 1 H),
7.03 (m, 2 H), 6.63 (d, J = 1.3 Hz, 1 H), 5.51 (t, J = 9.6 Hz, 1 H), 4.82
(dd, J = 9.4, 4.2 Hz, 1 H), 4.64 (dd, J = 4.4, 1.5 Hz, 1 H), 4.29 (m, 1
H), 4.25 (dd, J = 12.2, 4.4 Hz, 1 H), 4.17 (dd, J = 11.9, 1.8 Hz, 1 H),
3.96 (s, 3 H), 2.11 (s, 6 H), 2.08 (s, 3 H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 170.6, 169.8, 169.3, 163.7, 159.5, 134.7, 132.4, 120.3,
8.32 (dt, J = 7.9, 1.8 Hz, 1 H), 7.47 (dd, J = 7.9, 4.8 Hz, 1 H), 6.68 (d,
J = 1.2 Hz, 1 H), 5.54 (t, J = 9.4 Hz, 1 H), 4.72 (dd, J = 4.2, 1.5 Hz, 1
H), 4.69 (dd, J = 9.4, 4.4 Hz, 1 H), 4.27 (dd, J = 11.6, 3.9 Hz, 1 H),
4.22 (ddd, J = 11.7, 5.9, 1.5 Hz, 1 H), 4.19 (dd, J = 11.6, 9.7 Hz, 1 H),
2.13 (s, 3 H), 2.12 (s, 3 H), 2.10 (s, 3 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 170.7, 169.8, 169.3, 162.5, 154.3, 151.0, 137.4, 124.7,
118.1, 112.0, 94.7, 71.4, 68.6, 67.2, 61.8, 55.8, 27.6, 20.9, 20.7, 123.6, 95.6, 71.9, 68.7, 66.9, 61.7, 26.7, 20.9, 20.7, 20.6 ppm. HRMS
20.6 ppm. HRMS (ESI): calcd. for C20H23INaO10+ [M + Na]+ 573.02281;
found 573.02081.
(ESI): calcd. for C18H21INO9 [M + H]+ 522.02555; found 522.02452.
+
Compound 36: Following the general procedure using isonicotinic
acid, and purifying by silica gel column chromatography gave 36
(88 mg, 94 %; dr = 94:06) as a pale yellow solid, m.p. 116 °C. 1H
Compound 31: Following the general procedure using p-anisic
acid, and purifying by silica gel column chromatography gave 31
(91 mg, 92 %; dr = 76:24) as a pale yellow solid, m.p. 109 °C. 1H NMR (500 MHz, CDCl3): δ = 8.86 (d, J = 4.7 Hz, 1 H), 7.87 (d, J =
NMR (500 MHz, CDCl3): δ = 7.02 (d, J = 8.8 Hz, 2 H), 6.97 (d, J =
5.9 Hz, 1 H), 6.66 (br. s, 1 H), 5.54 (t, J = 9.3 Hz, 1 H), 4.71–4.68 (m,
8.8 Hz, 2 H), 6.62 (br. s, 1 H), 5.51 (t, J = 9.4 Hz, 1 H), 4.73 (dd, J = 2 H), 4.26 (dd, J = 12.0, 7.9 Hz, 1 H), 4.23–4.18 (m, 2 H), 2.13 (s, 3
9.4, 4.2 Hz, 1 H), 4.68 (dd, J = 4.2, 1.3 Hz, 1 H), 4.27 (m, 1 H), 4.25–
4.12 (m, 3 H), 3.89 (s, 3 H), 2.12 (s, 3 H), 2.11 (s, 3 H), 2.09 (s, 3 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 170.6, 169.9, 169.3, 164.2,
163.3, 132.4, 132.1, 120.8, 114.0, 113.9, 94.9, 71.6, 68.8, 67.1, 61.8,
H), 2.12 (s, 3 H), 2.10 (s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ =
170.7, 170.0, 169.3, 162.4, 150.8, 135.9, 122.9, 95.9, 71.9, 68.6, 66.8,
+
61.6, 26.4, 20.9, 20.7, 20.6 ppm. HRMS (ESI): calcd. for C18H21INO9
[M + H]+ 522.02555; found 522.02457.
+
55.5, 27.4, 20.9, 20.7, 20.6 ppm. HRMS (ESI): calcd. for C20H23INaO10
Compound 37: Following the general procedure using cyclohex-
anecarboxylic acid, and purifying by silica gel column chromatogra-
[M + Na]+ 573.02281; found 573.02075.
Compound 32: Following the general procedure using 4-butoxy- phy gave 37 (84 mg, 89 %; dr = 80:20) as a white semi-solid. 1H
benzoic acid, and purifying by silica gel column chromatography
gave 32 (94 mg, 88 %; dr = 86:14) as a pale yellow solid, m.p. 88 °C.
1H NMR (500 MHz, CDCl3): δ = 8.05 (d, J = 8.8 Hz, 2 H), 6.93 (d, J =
8.8 Hz, 2 H), 6.62 (d, J = 1.0 Hz, 1 H), 5.53 (t, J = 9.6 Hz, 1 H), 4.74
(dd, J = 9.4, 4.4 Hz, 1 H), 4.68 (dd, J = 4.2, 1.3 Hz, 1 H), 4.26 (dd, J =
12.0, 4.2 Hz, 1 H), 4.21 (m, 1 H), 4.18 (dd, J = 12.0, 2.1 Hz, 1 H), 4.03
(t, J = 6.5 Hz, 3 H), 2.12 (s, 3 H), 2.11 (s, 3 H), 2.09 (s, 3 H), 1.80 (m,
2 H), 1.54–1.47 (m, 2 H), 0.99 (t, J = 7.4 Hz, 3 H) ppm. 13C NMR
(125 MHz, CDCl3): δ = 170.7, 169.9, 169.3, 163.6, 163.4, 132.3, 132.1,
121.4, 114.4, 114.2, 94.9, 71.5, 68.9, 68.0, 67.9, 67.1, 61.8, 31.1, 27.5,
NMR (400 MHz, CDCl3): δ = 6.39 (br. s, 1 H), 5.46 (t, J = 9.6 Hz, 1 H),
4.59 (dd, J = 9.4, 4.2 Hz, 1 H), 4.53 (dd, J = 4.2, 1.4 Hz, 1 H), 4.22
(dd, J = 12.3, 4.6 Hz, 1 H), 4.16 (dd, J = 12.3, 9.9 Hz, 1 H), 4.11 (ddd,
J = 9.9, 4.5, 2.4 Hz, 1 H), 2.41–2.29 (m, 1 H), 2.12 (s, 3 H), 2.11 (s, 3
H), 2.08 (s, 3 H), 1.95–1.20 (m, 10 H) ppm. 13C NMR (100 MHz, CDCl3):
δ = 173.1, 170.7, 169.9, 169.3, 94.4, 71.5, 68.8, 67.0, 61.9, 42.8, 29.7,
28.7, 25.7, 25.3, 20.9, 20.7, 20.6 ppm. HRMS (ESI): calcd. for
C19H31INO9 [M + NH4]+ 544.10380; found 544.10321.
+
Compound 38: Following the general procedure using octanoic
acid, and purifying by silica gel column chromatography gave 38
+
20.9, 20.7, 20.6, 19.2, 13.8 ppm. HRMS (ESI): calcd. for C23H29INaO10
1
(92 mg, 94 %; dr = 83:17) as a white semi-solid. H NMR (400 MHz,
[M + Na]+ 615.06976; found 615.06828.
CDCl3): δ = 6.40 (d, J = 1.3 Hz, 1 H), 5.45 (t, J = 9.6 Hz, 1 H), 4.59
(dd, J = 9.4, 4.4 Hz, 1 H), 4.53 (dd, J = 4.2, 1.5 Hz, 1 H), 4.22 (dd, J =
12.3, 4.6 Hz, 1 H), 4.16 (dd, J = 12.3, 2.4 Hz, 1 H), 4.11 (ddd, J = 9.9,
4.5, 2.4 Hz, 1 H), 2.40 (t, J = 7.5 Hz, 2 H), 2.12 (s, 3 H), 2.11 (s, 3 H),
2.07 (s, 3 H), 1.68–0.83 (m, 14 H) ppm. 13C NMR (100 MHz, CDCl3):
δ = 171.0, 170.7, 169.9, 169.3, 94.5, 71.4, 68.8, 67.0, 61.8, 34.0, 31.6,
29.7, 28.9, 28.8, 24.7, 22.6, 20.9, 20.7, 20.6, 14.0 ppm. HRMS (ESI):
Compound 33: Following the general procedure using 2,3,4-tri-
methoxybenzoic acid, and purifying by silica gel column chroma-
tography gave 33 (94 mg, 86 %; dr = 70:30) as a pale yellow solid,
1
m.p. 95 °C. H NMR (500 MHz, CDCl3): δ = 7.31 (s, 2 H), 6.58 (d, J =
1.3 Hz, 1 H), 5.53 (t, J = 9.6 Hz, 1 H), 4.78 (dd, J = 9.6, 4.2 Hz, 1 H),
4.68 (dd, J = 4.2, 1.6 Hz, 1 H), 4.28–4.24 (m, 1 H), 4.23–4.17 (m, 2 H),
3.94 (s, 6 H), 3.93 (s, 3 H), 2.13 (s, 3 H), 2.12 (s, 3 H), 2.09 (s, 3 H)
ppm. 13C NMR (125 MHz, CDCl3): δ = 170.6, 169.8, 169.3, 163.3,
153.1, 143.2, 123.4, 107.3, 95.2, 71.7, 68.5, 67.1, 61.7, 60.9, 56.3, 27.2,
20.9, 20.7, 20.6 ppm. HRMS (ESI): calcd. for C22H27INaO12+ [M + Na]+
633.04394; found 633.04528.
calcd. for C20H31INaO9 [M + Na]+ 565.09050; found 565.08933.
+
Compound 39: Following the general procedure using phenoxy-
acetic acid, and purifying by silica gel column chromatography gave
1
39 (89 mg, 90 %; dr = 75:25) as a white solid, m.p. 124 °C. H NMR
(400 MHz, CDCl3): δ = 7.32 (td, J = 7.4, 1.2 Hz, 2 H), 7.02 (t, J =
7.4 Hz, 1 H), 6.94 (dt, J = 7.8, 0.9 Hz, 2 H), 6.48 (d, J = 1.2 Hz, 1 H),
5.40 (t, J = 9.9 Hz, 1 H), 4.76 (d, J = 1.9 Hz, 1 H), 4.55 (dd, J = 4.4,
1.5 Hz, 1 H), 4.44 (dd, J = 9.5, 4.4 Hz, 1 H), 4.11 (dd, J = 12.5, 8.3 Hz,
1 H), 4.03 (dd, J = 12.8, 2.4 Hz, 1 H), 3.73 (ddd, J = 10.0, 4.1, 2.4 Hz,
Compound 34: Following the general procedure using picolinic
acid, and purifying by silica gel column chromatography gave 34
(87 mg, 93 %) as a white solid, m.p. 145 °C. 1H NMR (400 MHz,
CDCl3): δ = 8.80 (ddd, J = 4.7, 1.2, 0.8 Hz, 1 H), 8.14 (dt, J = 6.8,
0.9 Hz, 1 H), 8.14 (td, J = 7.8, 1.7 Hz, 1 H), 7.55 (ddd, J = 7.7, 4.7, 1 H), 2.10 (s, 6 H), 2.06 (s, 3 H) ppm. 13C NMR (125 MHz, CDCl3): δ =
1.2 Hz, 1 H), 6.70 (d, J = 1.4 Hz, 1 H), 5.54 (t, J = 9.5 Hz, 1 H), 4.79
(dd, J = 9.2, 4.4 Hz, 1 H), 4.75 (dd, J = 4.4, 1.5 Hz, 1 H), 4.33 (ddd,
J = 10.0, 4.2, 2.5 Hz, 1 H), 4.27 (dd, J = 12.2, 7.9 Hz, 1 H), 4.16 (dd,
J = 12.2, 2.2 Hz, 1 H), 2.13 (s, 3 H), 2.12 (s, 3 H), 2.08 (s, 3 H) ppm.
13C NMR (100 MHz, CDCl3): δ = 170.7, 169.9, 169.3, 162.5, 150.2,
146.7, 137.1, 127.6, 125.6, 95.9, 71.7, 68.8, 67.0, 61.7, 27.1, 20.9, 20.7,
170.6, 169.8, 169.2, 166.4, 157.5, 129.8, 122.1, 114.6, 95.3, 71.6, 68.5,
66.6, 64.9, 61.5, 26.6, 20.9, 20.7, 20.6 ppm. HRMS (ESI): calcd. for
C20H27INO10 [M + NH4]+ 568.06742; found 568.06711.
+
Compound 40: Following the general procedure using Fmoc-β-Ala-
OH, and purifying by silica gel column chromatography gave 40
(116 mg, 91 %) as a white solid, m.p. 92 °C. 1H NMR (400 MHz,
CDCl3): δ = 7.77 (d, J = 7.5 Hz, 2 H), 7.59 (d, J = 7.4 Hz, 2 H), 7.40 (t,
J = 7.4 Hz, 2 H), 7.32 (t, J = 7.6 Hz, 2 H), 6.42 (br. s, 1 H), 5.47 (t, J =
20.6 ppm. HRMS (ESI): calcd. for C18H20INNaO9 [M + Na]+
+
544.00750; found 544.00567.
Compound 35: Following the general procedure using nicotinic 9.2 Hz, 1 H), 5.35 (t, J = 4.8 Hz, 1 H), 4.57–4.53 (m, 2 H), 4.40 (d, J =
acid, and purifying by silica gel column chromatography gave 35
(91 mg, 97 %) as a white solid, m.p. 127 °C. 1H NMR (500 MHz,
CDCl3): δ = 9.27 (d, J = 1.9 Hz, 1 H), 8.86 (dd, J = 4.7, 1.5 Hz, 1 H),
6.1 Hz, 2 H), 4.24–4.10 (m, 3 H), 3.52 (q, J = 5.8 Hz, 2 H), 2.68 (t, J =
5.2 Hz, 2 H), 2.11 (s, 3 H), 2.10 (s, 3 H), 2.04 (s, 3 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 170.6, 169.9, 169.8, 169.3, 156.3, 143.8, 143.7,
Eur. J. Org. Chem. 2016, 291–301
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