4.1 Hz, 1H), 3.66 (dd, J = 12.4, 2.9 Hz, 1H), 2.82 (ddd, J = 13.0,
13.0, 8.1 Hz, 1H), 2.48–2.28 (m, 5H), 2.10–1.99 (m, 2H). 13C
NMR (CDCl3) 100 MHz: δ 174.0, 173.8, 140.9, 140.5, 138.0,
131.0, 128.9, 128.2, 127.5, 127.4, 127.2, 60.6, 60.3, 51.7, 37.8,
34.2, 28.7, 25.9. TOF HRMS: m/z calcd for C23H24O4 [M+H]+:
365.1753; found: 365.1737.
137.1, 136.3, 134.3, 131.2, 128.7, 128.5, 127.5, 123.7, 60.7, 60.3,
51.6, 37.8, 34.1, 28.6, 25.9. TOF HRMS: m/z calcd for
C22H23NO4 [M+H]+: 366.1705; found: 366.1694.
4.1.5.6. Compound 10f
This compound was prepared by using the general procedure
for Suzuki reactions with compound 9f to give compound 10f as
a white solid (28 mg, 56% yield). mp 144.3-145.2 °C. Rf 0.61
4.1.5.2. Compound 10b
1
This compound was prepared by using the general procedure
for Suzuki reactions with compound 10b to give compound 10b
as a white solid (26 mg, 47% yield). mp 113.2-114.2 °C. Rf 0.74
(pure EtOAc). H NMR (CDCl3) 300 MHz: 8.64 (s, 2H), 7.59
(d, J = 8.3 Hz, 2H), 7.53–7.43 (m, 4H), 5.64–5.48 (m, 2H), 4.55
(ddd, J = 11.0, 8.2, 6.5 Hz, 1H), 4.45 (ddd, J = 11.2, 8.2, 6.5 Hz,
1H), 4.02 (dt, J = 11.2, 4.2 Hz, 1H), 3.86 (dt, J = 11.2, 4.1 Hz,
1H), 3.66 (dd, J = 12.4, 2.9 Hz, 1H), 2.80 (ddd, J = 13.0, 13.0, 7.9
Hz, 1H), 2.48–2.24 (m, 5H), 2.08–2.00 (m, 2H). 13C NMR
(CDCl3) 75 MHz: δ 173.8, 173.7, 150.4, 147.9, 140.0, 137.4,
131.3, 128.6, 127.4, 121.6, 60.7, 60.3, 51.7, 37.8, 34.1, 28.6,
25.9. TOF HRMS: m/z calcd for C22H23NO4 [M+H]+: 366.1705;
found: 366.1700.
1
(30% EtOAc/Hex). H NMR (CDCl3) 400 MHz: 7.40 (d, J =
8.1 Hz, 2H), 7.08 (d, J = 8.2 Hz, 2H), 6.93 (s, 2H), 5.63–5.51 (m,
2H), 4.65–4.53 (m, 1H), 4.52–4.42 (m, 1H), 4.03 (dt, J = 11.1,
4.2 Hz, 1H), 3.90 (dt, J = 11.1, 4.1 Hz, 1H), 3.65 (dd, J = 12.5,
2.8 Hz, 1H), 2.82 (ddd, J = 12.9, 12.9, 7.9 Hz, 1H), 2.47–2.30 (m,
5H), 2.32 (s, 3H), 2.11–2.02 (m, 2H), 1.98 (s, 6H). 13C NMR
(CDCl3) 100 MHz: δ 174.3, 173.8, 140.2, 138.7, 137.1, 136.7,
136.2, 130.9, 129.7, 129.0, 128.2, 127.7, 60.5, 60.3, 51.7, 37.9,
34.2, 28.7, 25.9, 21.1, 20.9. TOF HRMS: m/z calcd for C26H30O4
[M+H]+: 407.2222; found: 407.2189.
4.1.5.7. Compound 10g
This compound was prepared by using the general procedure
for Suzuki reactions with compound 9g to give compound 10g as
a white solid (46 mg, 93% yield). mp 145.7-146.6 °C. Rf 0.68
4.1.5.3. Compound 10c
1
This compound was prepared by using the general procedure
for Suzuki reactions with compound 10c to give compound 10c
as a white solid (27 mg, 52% yield). mp 151.6-152.3. °C Rf 0.25
(75% EtOAc/Hex). H NMR (CDCl3) 300 MHz: 9.18 (s, 1H),
8.91 (s, 2H), 7.53 (s, 4H), 5.63–5.47 (m, 2H), 4.58–4.50 (m, 1H),
4.48-4.40 (m, 1H), 4.02 (dt, J = 11.2, 4.2 Hz, 1H), 3.86 (dt, J =
11.2, 4.1 Hz, 1H), 3.66 (dd, J = 12.4, 2.9 Hz, 1H), 2.79 (ddd, J =
12.9, 12.9, 8.0 Hz, 1H), 2.46–2.28 (m, 5H), 2.08–2.00 (m, 2H).
13C NMR (CDCl3) 75 MHz: δ 173.7, 173.6, 157.6, 154.9, 140.0,
134.0, 133.5, 131.3, 128.9, 128.5, 127.3, 60.9, 60.3, 51.7, 37.8,
34.1, 28.6, 25.9. TOF HRMS: m/z calcd for C21H22N2O4
[M+H]+: 367.1658; found: 367.1663.
1
(30% EtOAc/Hex). H NMR (CDCl3) 300 MHz: 7.51 (d, J =
8.0 Hz, 2H), 7.42 (d, J = 8.0 Hz, 2H), 7.32–7.24 (m, 1H), 7.15–
7.04 (m, 2H), 6.84 (dd, J = 8.0, 2.5 Hz, 1H), 5.95–5.70 (br, 1H),
5.63–5.48 (m, 2H), 4.61–4.51 (m, 1H), 4.51–4.41 (m, 1H), 4.03
(dt, J = 11.2, 4.2 Hz, 1H), 3.87 (dt, J = 11.2, 4.1 Hz, 1H), 3.63
(dd, J = 12.5, 2.9 Hz, 1H), 2.79 (ddd, J = 12.9, 12.9, 7.8 Hz, 1H),
2.51–2.22 (m, 5H), 2.08–2.00 (m, 2H). 13C NMR (CDCl3) 75
MHz: δ 174.4, 174.2, 156.4, 142.5, 140.1, 138.0, 131.0, 130.1,
128.9, 128.2, 127.4, 119.5, 114.5, 114.1, 60.7, 60.4, 51.6, 37.8,
34.2, 28.7, 25.8. TOF HRMS: m/z calcd for C23H24O5 [M+H]+:
381.1702; found: 381.1680.
4.1.5.8. Compound 10h
This compound was prepared by using the general procedure
for Suzuki reactions with compound 9h to give compound 10h as
a white solid (57 mg, 98% yield). mp 114.3-114.7 °C. Rf 0.36
1
(30% EtOAc/Hex). H NMR (CDCl3) 400 MHz: 7.56 (d, J =
4.1.5.4. Compound 10d
8.4 Hz, 2H), 7.47 (d, J = 8.3 Hz, 2H), 6.92 (s, 1H), 5.65–5.48 (m,
2H), 4.55 (ddd, J = 11.1, 8.5, 6.7 Hz, 1H), 4.45 (ddd, J = 11.2,
8.2, 6.5 Hz, 1H), 4.08 (s, 6H), 4.02 (dt, J = 11.2, 4.1 Hz, 1H),
3.86 (dt, J = 11.2, 4.1 Hz, 1H), 3.65 (dd, J = 12.4, 2.9 Hz, 1H),
2.79 (ddd, J = 13.0, 13.0, 8.3 Hz, 1H), 2.48–2.27 (m, 5H), 2.10–
1.99 (m, 2H). 13C NMR (CDCl3) 75 MHz: δ 173.7, 162.7, 159.5,
140.2, 133.7, 132.6, 131.2, 129.3, 128.6, 128.0, 119.1, 60.7, 60.2,
54.9, 54.6, 51.7, 37.7, 34.1, 28.6, 25.8. TOF HRMS: m/z calcd
for C23H26N2O4 [M+H]+: 427.1869; found: 427.1882.
This compound was prepared by using the general procedure
for Suzuki reactions with compound 9d to give compound 10d as
a white solid (34 mg, 61% yield). mp 117.2-117.9 °C. Rf 0.51
1
(30% EtOAc/Hex). H NMR (CDCl3) 300 MHz: 7.51 (d, J =
8.0 Hz, 2H), 7.39 (d, J = 8.0 Hz, 2H), 7.29–7.22 (m, 1H), 6.89 (d,
J = 7.7 Hz, 1H), 6.87 (s, 1H), 6.73-6.70 (m, 1H), 5.61–5.45 (m,
2H), 4.57–4.48 (m, 1H), 4.46–4.37 (m, 1H), 3.98 (dt, J = 11.2,
4.2 Hz, 1H), 3.82 (dt, J = 11.2, 4.1 Hz, 1H), 3.61 (dd, J = 12.5,
2.8 Hz, 1H), 2.96 (s, 6H), 2.77 (ddd, J = 12.9, 12.9, 7.8 Hz, 1H),
2.43–2.25 (m, 5H), 2.04–1.96 (m, 2H). 13C NMR (CDCl3) 75
MHz: δ 174.1, 173.8, 150.9, 142.0, 141.5, 137.8, 131.01, 129.6,
129.0, 128.0, 127.7, 116.0, 111.9, 111.7, 60.6, 60.3, 51.7, 40.9,
37.8, 34.2, 28.7, 25.9. TOF HRMS: m/z calcd for C25H29NO4
[M+H]+: 408.2175; found: 408.2155.
4.1.5.9. Compound 10i
This compound was prepared by using the general procedure
for Suzuki reactions with compound 9i to give compound 10i as
a white solid (34 mg, 61% yield). mp 150.7-151.3 °C. Rf 0.58
1
(30% EtOAc/Hex). H NMR (CDCl3) 400 MHz: 8.29 (s, 1H),
7.66 (d, J = 8.2 Hz, 2H), 7.48 (d, J = 8.3 Hz, 2H), 7.39 (dt, J =
8.2, 1.0 Hz, 1H), 7.27–7.23 (m, 2H), 7.17 (dd, J = 7.3, 1.0 Hz,
1H), 6.78–6.66 (m, 1H), 5.65-5.53 (m, 2H), 4.65–4.53 (m, 1H),
4.53–4.41 (m, 1H), 4.04 (dt, J = 11.2, 4.2 Hz, 1H), 3.89 (dt, J =
11.2, 4.1 Hz, 1H), 3.69 (dd, J = 12.5, 2.9 Hz, 1H), 2.85 (ddd, J =
12.8, 12.8, 7.9 Hz, 1H), 2.47–2.28 (m, 5H), 2.16–1.97 (m, 2H).
13C NMR (CDCl3) 100 MHz: δ 174.2, 173.8, 140.5, 137.4, 136.4,
134.0, 130.9, 129.0, 129.0, 127.9, 126.2, 124.6, 122.3, 119.7,
110.4, 102.1, 60.6, 60.4, 51.7, 37.8, 34.2, 28.7, 25.9. TOF
HRMS: m/z calcd for C25H25NO4 [M+H]+: 404.1862; found:
404.1832.
4.1.5.5. Compound 10e
This compound was prepared by using the general procedure
for Suzuki reactions with compound 9e to give compound 10e as
a white solid (41 mg, 83% yield). mp 132.6-133.5 °C. Rf 0.36
1
(50% EtOAc/Hex). H NMR (CDCl3) 400 MHz: 8.82 (s, 1H),
8.57 (s, 1H), 7.83 (d, J = 7.9 Hz, 1H), 7.50 (q, J = 8.0 Hz, 4H),
7.38–7.28 (m, 1H), 5.65–5.46 (m, 2H), 4.54 (dt, J = 10.7, 7.4 Hz,
1H), 4.44 (dt, J = 15.0, 7.8 Hz, 1H), 4.04–4.00 (m, 1H), 3.88–
3.83 (m, 1H), 3.65 (dd, J = 12.4, 2.8 Hz, 1H), 2.79 (ddd, J = 13.0,
13.0, 8.1 Hz, 1H), 2.45–2.27 (m, 5H), 2.06–2.00 (m, 2H). 13C
NMR (CDCl3) 100 MHz: δ 173.9, 173.7, 148.6, 148.4, 138.9,
4.1.5.10. Compound 10j