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Organic & Biomolecular Chemistry
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141.5, 137.7, 132.7, 131.0, 128.9, 128.6, 128.5, 128.4, 127.9, 127.6, Compound 17. According to General Procedure B, the desired (±)-
DOI: 10.1039/C8OB00644J
127.3, 127.1, 126.3, 126.2, 122.9, 115.5, 109.7, 93.3, 57.6. MS, m/z 2,3-trans-dihybenzofuran 17 (66 mg, 0.16 mmol, white solid,
ESI = 389.0 [M-H]-. Data in agreements with those reported in isolated yield: 66 %) was obtained from compound 6 (100 mg, 0.45
literature.52
mmol) and laccase (20.0 U). 1H-NMR (400 MHz; [D1]CHCl3, r.t.):
Compound 13. According to General Procedure B, the desired (±)- 7.40 (dd, J = 8.3, 1.8 Hz, 1H), 7.26-7.19 (m, J = 4.2 Hz, 6H), 7.14 (bd, J
2,3-trans-dihybenzofuran 13 (60 mg, 0.14 mmol, white solid, = 7.6 Hz, 1H), 7.06-7.00 (m, 4H), 6.95 (d, J = 8.3 Hz, 1H), 6.90 (d, J =
isolated yield: 60 %) was obtained from compound 2 (95 mg, 0.45 16.3 Hz, 1H), 6.87-6.82 (AA'BB' system, 2H), 5.53 (d, J = 8.4 Hz, 1H),
mmol) and laccase (19.0 U). 1H-NMR (400 MHz; [D1]CHCl3, r.t.): δ 4.82 (s, 1H), 4.54 (d, J = 8.4 Hz, 1H), 2.37 (s, 3H), 2.36 (s, 3H). 13C-
7.39-7.34 (m, 2H), 7.26-7.22 (AA'BB' system, 2H), 7.19-7.10 (m, 6H), NMR (400 MHz; [D1]CHCl3
7.00 (d, J = 16.3 Hz, 1H), 6.94 (d, J = 8.3 Hz, 1H), 6.89 (d, J = 16.3 Hz, 137.8, 132.9, 131.2, 131.1, 128.9, 128.7, 128.5, 128.3, 128.1, 127.9,
1H), 6.86-6.82 (AA'BB' system, 2H), 5.49 (d, J = 8.6 Hz, 1H), 4.85 (s, 127.7, 127.6, 126.8, 126.4, 125.5, 123.4, 122.9, 115.6, 109.6, 97.3,
1H), 4.55 (d, J = 8.5 Hz, 1H), 2.39 (s, 3H), 2.36 (s, 3H). 13C-NMR (101 57.6, 30.9, 214.5, 21.4. MS, m/z ESI = 417.0 [M-H]-. Data in
MHz; [D1]CHCl3, r.t.): 159.5, 155.5, 138.5, 136.9, 136.9, 134.9, agreements with those reported in literature.53
132.8, 131.2, 129.6, 129.3, 128.3, 127.6, 127.6, 127.5, 126.2, 126.1, Compound 18. According to General Procedure B, the desired (±)-
122.8, 115.5, 109.6, 93.4, 57.3, 21.2, 21.1; HRMS (EI), calcd for 2,3-trans-dihybenzofuran 18 (23 mg, 0.06 mmol, white solid,
C30H25O2(M-): 417.1855, found: 417.1858; MS, m/z ESI =417.0 [M- isolated yield: 49 %) was obtained from compound 7 (50 mg, 0.23
H]-.
mmol) and laccase (9.5 U). 1H-NMR (400 MHz; [D1]CHCl3, r.t.):
Compound 14. According to General Procedure B, the desired (±)- 7.73-7.70 (bt, J = 1 Hz, 1H), 7.67 (dt, J = 8.0, 1.2 Hz, 1H); 7.64 (dt, J =
2,3-trans-dihybenzofuran 14 (37 mg, 0.08 mmol, white solid, 7.2, 1.2 Hz, 1H) 7.52-7.42 (m, 6H), 7.23-7.21 (AA'BB' system, 2H),
isolated yield: 74 %) was obtained from compound 3 (50 mg, 0.27 7.16 (s, 1H). 7.10 (d, J = 16.3 Hz, 1H), 7.00 (d, J = 8.3 Hz, 1H), 6.90-
mmol) and laccase (9.5 U). 1H-NMR (400 MHz; [D1]CHCl3, r.t.): δ 6.86 (m, 3H), 5.47 (d, J = 8.2 Hz, 1H), 4.64 (d, J = 8.2 Hz, 1H). 13C-
7.69-7.67 (AA'BB' system, 2H), 7.63-7.61 (AA'BB' system, 2H), 7.53- NMR (101 MHz; [D1]CHCl3, r.t.): 160.2, 156.1, 143.0, 138.8, 132.8,
7.51 (AA'BB' system, 2H), 7.46 (dd, J = 8.4, 1.5 Hz, 1H), 7.35-7.33 131.8, 131.6, 131.2, 130.8, 130.5, 130.3, 130.2, 129.8, 129.6, 129.4,
(AA'BB' system, 2H), 7.22-7.20 (AA'BB' system, 2H), 7.17-7.12 (m, 128.8, 127.5, 124.2, 123.1, 118.8, 118.5, 115.8, 113.2, 112.9, 110.3,
2H), 7.00 (d, J = 8.3 Hz, 1H), 6.92-6.86 (m, 3H), 5.48 (d, J = 8.3 Hz, 93.1, 57.2; HRMS (EI), calcd for C30H19N2O2 (M-): 439.1447, found:
1H), 5.17 (s, 1H), 4.66 (d, J = 8.3 Hz, 1H). 13C-NMR (101 MHz; 439.1445; MS, m/z ESI = 463.2 [M+Na]+.
[D1]CHCl3
Compound 19. According to General Procedure B, the desired (±)-
131.8, 131.6, 130.4, 130.0, 129.1, 129.1, 127.6, 126.5, 124.7, 124.7, 2,3-trans-dihybenzofuran 19 (23 mg, 0.05 mmol, white solid,
123.2, 119.0, 118.5, 115.7, 115.7, 111.5, 110.3, 110.3, 110.1, 93.1, isolated yield: 46 %) was obtained from compound 8 (50 mg, 0.21
57.7; HRMS (EI), calcd for C30H19N2O2 (M-): 439.1446, found: mmol) and laccase (8.7 U). 1H-NMR (400 MHz; [D1]CHCl3, r.t.):
439.1444; MS, m/z ESI = 463.2 [M+Na]+.
7.40 (dd, J = 8.3, 1.7 Hz, 1H), 7.35 (bs, 1H), 7.32-7.19 (m, 7H), 7.14
Compound 15. According to General Procedure B, the desired (±)- (dt, J = 6.7, 2.0 Hz, 1H), 7.10 (t, J = 1.7 Hz, 1H), 7.05 (d, J = 16.3 Hz,
2,3-trans-dihybenzofuran 15 (68 mg, 0.14 mmol, white solid, 1H), 6.99 (dt, J = 7.6, 1.3 Hz, 1H), 6.96 (d, J = 8.3 Hz, 1H), 6.88 (d, J =
isolated yield: 68 %) was obtained from compound 4 (100 mg, 0.45 16.3 Hz, 1H), 6.86-6.83 (AA'BB' system, 2H), 5.52 (d, J = 8.4 Hz, 1H),
1
mmol) and laccase (17.4 U). H-NMR (400 MHz; [D4]MeOH, r.t.): δ 4.54 (d, J = 8.4 Hz, 1H), 2.52 (s, 3H), 2.48 (s, 3H). 13C-NMR (101 MHz;
8.24-8.22 (AA'BB' system, 2H), 8.17-8.15 (AA'BB' system, 2H), 7.68- [D1]CHCl3, r.t.): 159.7, 155.7, 142.2, 139.3, 138.7, 138.3, 132.6,
7.66 (AA'BB' system, 2H), 7.54 (dd, J = 8.3, 1.8 Hz, 1H), 7.46-7.44 130.90, 130.74, 129.4, 129.06, 128.99, 128.1, 127.6, 126.3, 125.8,
(AA'BB' system, 2H), 7.32 (d, J = 16.3 Hz, 1H), 7.27 (bs, 1H), 7.19- 125.39, 125.24, 125.04, 124.4, 123.06, 123.02, 115.5, 109.8, 93.1,
7.17 (AA'BB' system, 2H), 7.06 (d, J = 16.4 Hz, 1H), 6.96 (d, J = 8.3 57.6, 15.9, 15.7; HRMS (EI), calcd for C30H25O2S2 (M-): 481.1296,
Hz, 1H), 6.81-6.79 (AA'BB' system, 2H), 5.52 (d, J = 8.4 Hz, 1H), 4.79 found: 481.1298; MS, m/z ESI = 481.1 [M-H]-.
(d, J = 8.3 Hz, 1H). 13C-NMR (101 MHz; [D4]MeOH, r.t.): 208.6, Compound 20. According to General Procedure B, the desired (±)-
160.5, 157.7, 149.1, 147.3, 146.3, 144.5, 132.7, 130.6, 130.5, 130.3, 2,3-trans-dihybenzofuran 20 (29 mg, 0.06 mmol, white solid,
129.1, 128.9, 127.3, 126.4, 123.8, 123.6, 123.5, 123.2, 115.1, 109.6, isolated yield: 58 %) was obtained from compound 9 (50 mg, 0.20
99.9, 93.3, 56.9; HRMS (EI), calcd for C28H19N2O6 (M-): 479.1243, mmol) and laccase (8.2 U). 1H-NMR (400 MHz; [D1]CHCl3, r.t.):
found: 479.1244; MS, m/z ESI = 479.0 [M-H]-.
7.39 (dd, J = 8.3, 1.7 Hz, 1H), 7.26-7.22 (m, 3H), 7.03 (d, J = 16.2 Hz,
Compound 16. According to General Procedure B, the desired (±)- 1H), 6.94 (d, J = 8.3 Hz, 1H), 6.86 (d, J = 16.2 Hz, 1H), 6.86-6.82
2,3-trans-dihybenzofuran 16 (33 mg, 0.07 mmol, white solid, (AA'BB' system, 2H), 6.64 (d, J = 2.2 Hz, 2H), 6.43 (t, J = 2.3 Hz, 1H),
isolated yield: 55 %) was obtained from compound 5 (60 mg, 0.27 6.39 (t, J = 2.2 Hz, 1H), 6.37 (d, J = 2.3 Hz, 2H), 5.54 (d, J = 8.3 Hz,
mmol) and laccase (9.3 U). 1H-NMR (400 MHz; [D1]CHCl3, r.t.): δ 1H), 4.50 (d, J = 8.3 Hz, 1H), 3.83 (s, 6H), 3.78 (s, 6H). 13C-NMR (101
7.41-7.39 (AA'BB' system, 2H), 7.36 (dd, J = 8.3, 1.0 Hz, 1H), 7.29- MHz; [D1]CHCl3, r.t.): 161.1, 160.9, 159.7, 155.8, 143.9, 139.7,
7.26 (m, 3H), 7.18-7.17 (m, 3H), 6.94-6.88 (m, 7H), 6.69-6.20 (AA'BB' 132.7, 130.8, 130.7, 129.0, 128.0, 127.6, 126.3, 123.1, 115.5, 109.7,
system, J = 6.9 Hz, 2H), 5.46 (d, J = 8.7 Hz, 1H), 4.54 (d, J = 8.7 Hz, 106.5, 104.3, 99.7, 99.1, 93.0, 57.8, 55.3, 55.3. MS, m/z ESI = 509.3
1H), 3.84 (s, 3H), 3.83 (s, 3H). 13C-NMR (101 MHz; [D1]CHCl3, r.t.): [M-H]-. Data in agreements with those reported in literature.52
159.3, 159.9, 158.8, 155.6, 133.4, 132.6, 131.3, 131.6, 130.5, 129.4, Compound 21. According to General Procedure B, the desired (±)-
127.6, 127.5, 127.3, 126.5, 125.9, 122.6, 115.5, 114.3, 114.1, 109.6, 2,3-trans-dihybenzofuran 21 (34 mg, 0.08 mmol, white solid,
93.5, 56.9, 55.3, 55.3. MS, m/z ESI = 449.0 [M-H]-. Data in isolated yield: 58 %) was obtained from compound 10 (50 mg, 0.22
agreements with those reported in literature. 52
mmol), and laccases (9.4 U). H-NMR (400 MHz; [D1]CHCl3, r.t.):
1
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