Spectral data comparison table of compound p5 with paulomycin A1

Position / 1H NMR of paulomycin A / 1H NMR of p5 / 13C NMR of paulomycin A / 13C NMR of p5
1 / ----- / ----- / 169.35 / 170.0
2 / ----- / ----- / 100.72 / 101.1
3 / ----- / ----- / 159.37 / 160.2
4 / ----- / ----- / 198.50 / 199.4
5 / 3.16, 3.23 (AB) / 3.19, 3.32 (ABq, 18.0) / 48.01 / 48.7
6 / ----- / ----- / 78.20 / 78.9
7 / ----- / ----- / 188.39 / 189.1
8 / 3.83 (d) / 3.84 (d, 10) / 78.26 / 79.0
9 / 3.70 (ddd) / 3.72 (ddd, 10, 6, 2.5) / 69.20 / 69.9
10 / 4.31 (dd) / 4.31 (dd, 2, 2) / 76.18 / 76.9
11 / 4.82 (dd) / 4.82 (dd, 10, 2) / 70.73 / 71.5
12 / 4.18 (ddd) / 4.19 (ddd, 10, 4.5, 2.5) / 72.29 / 73.0
13 / 3.88, 3.99 (ABX) / 3.88, 3.99 (ABX, 12.5, 4.5, 2) / 62.30 / 62.9
1’ / 4.95 (dd) / 4.95 (dd, 4, 2) / 99.04 / 99.8
2’ / 1.90, 2.22 (ABMX) / 1.90, 2.22 (ABMX, 13, 6, 2) / 30.56 / 31.3
3’ / 3.65 (dd) / 3.65 (dd, 11, 5) / 74.40 / 75.1
3’-OMe / 3.33 (s) / 3.34 (s) / 56.62 / 57.3
4’ / ----- / ----- / 73.62 / 74.3
5’ / 4.52 (q) / 4.52 (q, 6.5) / 67.18 / 68.5
6’ / 1.27 (d) / 1.29 (d, 6.5) / 15.28 / 16.0
7’ / 5.36 (q) / 5.36 (q, 6.5) / 69.93 / 70.6
8’ / 1.22 (d) / 1.24 (d, 6.5) / 15.39 / 16.1
1’’ / ----- / ----- / 160.25 / 160.9
2’’ / ----- / ----- / 123.36 / 124.1
3’’ / 6.83 (q) / 6.83 (q, 6.5) / 136.64 / 137.4
4’’ / 1.97 (d) / 1.95 (d, 6.5) / 14.11 / 14.8
5’’ / ----- / ----- / 142.64 / 143.3
1’’’ / ----- / ----- / 175.15 / 175.9
2’’’ / 2.45 (ddq) / 2.45 (ddq, 7, 6, 1.5) / 41.51 / 42.2
3’’’ / 1.50, 1.70 (ABMX3) / 1.53, 1.72 (ABMX3, 13, 7, 7) / 26.65 / 27.4
4’’’ / 0.94 (t) / 0.97 (t, 7) / 11.39 / 12.1
5’’’ / 1.17 (d) / 1.18 (d, 7) / 16.73 / 17.5
1’’’’ / ----- / ----- / 170.18 / 170.9
2’’’’ / 1.98 (s) / 1.99 (s) / 19.99 / 20.7

Spectral data comparison table of compound p4 with paulomycin B1

Position / 1H NMR of paulomycin B / 1H NMR of p4 / 13C NMR of paulomycin B / 13C NMR of p4
1 / ----- / ----- / 169.35 / 170.1
2 / ----- / ----- / 100.14 / 100.9
3 / ----- / ----- / 159.36 / 160.2
4 / ----- / ----- / 198.37 / 199.1
5 / 3.15, 3.35 (AB) / 3.19, 3.29 (ABq, 18.0) / 47.95 / 48.7
6 / ----- / ----- / 78.15 / 79.0
7 / ----- / ----- / 188.40 / 189.1
8 / 3.86 (d) / 3.84 (d, 10) / 78.14 / 78.9
9 / 3.70 (ddd) / 3.72 (ddd, 13, 7, 2.5) / 69.28 / 70.1
10 / 4.28 (dd) / 4.31 (dd, 3.5, 3) / 75.91 / 76.8
11 / 4.81 (dd) / 4.82 (dd, 14, 3) / 70.71 / 71.5
12 / 4.21 (ddd) / 4.20 (ddd, 14, 6.5, 3) / 72.21 / 73.0
13 / 3.86, 3.99 (ABX) / 3.88, 3.99 (ABX, 16, 6.5, 4.0) / 62.23 / 62.9
1’ / 4.93 (dd) / 4.95 (dd, 4, 2) / 98.34 / 99.7
2’ / 1.90, 2.23 (ABMX) / 1.89, 2.22 (ABMX, 16, 5, 2) / 30.33 / 31.3
3’ / 3.65 (dd) / 3.66 (dd, 11.5, 6) / 74.38 / 75.2
3’-OMe / 3.33 (s) / 3.34 (s) / 56.69 / 57.3
4’ / ----- / ----- / 73.66 / 74.4
5’ / 4.58 (q) / 4.52 (q, 8) / 67.65 / 68.5
6’ / 1.28 (d) / 1.28 (d, 8) / 15.23 / 15.9
7’ / 5.39 (q) / 5.35 (q, 8) / 69.96 / 70.7
8’ / 1.19 (d) / 1.23 (d, 8) / 15.44 / 16.2
1’’ / ----- / ----- / 160.25 / 161.0
2’’ / ----- / ----- / 123.32 / 124.1
3’’ / 6.88 (q) / 6.83 (q, 9.0) / 136.66 / 137.4
4’’ / 1.97 (d) / 1.95 (d, 9.0) / 14.13 / 14.8
5’’ / ----- / ----- / 142.54 / 143.4
1’’’ / ----- / ----- / 175.71 / 176.4
2’’’ / 2.65 (ddq) / 2.63 (ddq, 9, 4) / 34.15 / 34.9
3’’’ / 1.19 (d) / 1.21 (d, 8.5) / 18.93 / 19.6
4’’’ / 1.17 (d) / 1.19 (d, 9.5) / 18.77 / 19.5
5’’’ / ----- / ----- / ----- / -----
1’’’’ / ----- / ----- / 170.18 / 170.9
2’’’’ / 2.02 (s) / 1.99 (s) / 19.98 / 20.7

Spectral data comparison table of compound p2 with paulomenolA2,3

Position / 1H NMR of paulomenol A / 1H NMR of p2 / 13C NMR of paulomenol A / 13C NMR of p2
1 / ----- / ----- / 170.01 / 170.1
2 / ----- / ----- / 100.53 / 100.7
3 / ----- / ----- / 160.01 / 160.2
4 / ----- / ----- / 197.60 / 199.4
5 / 3.16 (dd) / 3.10, 3.20 (ABq, 20) / 48.76 / 48.9
6 / ----- / ----- / 78.98 / 79.1
7 / ----- / ----- / 188.66 / 188.8
8 / 3.92 (d, 8) / 3.88 (d, 8) / 78.98 / 79.1
9 / 3.49 (m) / 3.52-3.44 (m) / 68.58 / 68.7
10 / 4.10 (m) / 4.11-4.07 (m) / 81.37 / 81.5
11 / 3.49 (m) / 3.52-3.44 (m) / 70.34 / 70.5
12 / 4.08 (m) / 4.07-4.04 (m) / 75.72 / 75.9
13 / 3.73 (m) / 3.75, 3.79 (ABX, 13, 7, 2) / 64.04 / 64.2
1’ / 5.17 (q) / 5.15 (dd, 5, 2) / 100.3 / 100.5
2’ / 1.92, 2.27 (m) / 1.92, 2.27 (ABMX, 16, 6, 3) / 30.91 / 31.0
3’ / 3.65 (m) / 3.66 (dd, 13, 7) / 75.02 / 75.1
3’-OMe / 3.34 (s) / 3.32 (s) / 57.26 / 57.3
4’ / ----- / ----- / 74.23 / 74.3
5’ / 4.49 (q, 6) / 4.47 (q, 8) / 68.24 / 68.4
6’ / 1.29 (d, 6) / 1.27 (d, 7) / 15.99 / 16.1
7’ / 5.39 (q, 6.5) / 5.37 (q, 8.5) / 70.59 / 70.7
8’ / 1.31 (d, 6.5) / 1.29 (d, 7) / 15.98 / 17.4
1’’ / ----- / ----- / ----- / -----
2’’ / ----- / ----- / ----- / -----
3’’ / ----- / ----- / ----- / -----
4’’ / ----- / ----- / ----- / -----
5’’ / ----- / ----- / ----- / -----
1’’’ / ----- / ----- / 175.07 / 175.8
2’’’ / 2.46 (m) / 2.45 (ddq, 12, 8, 2) / 42.15 / 42.3
3’’’ / 1.64 (m) / 1.53, 1.73 (ABMX3, 16, 9, 4.5) / 27.32 / 27.5
4’’’ / 0.98 (t, 6)) / 0.96 (t, 9) / 11.87 / 12.1
5’’’ / 1.21 (d, 8) / 1.19 (d, 9) / 15.99 / 16.1
1’’’’ / ----- / ----- / 171.5 / 171.2
2’’’’ / 2.04 (s) / 2.02 (s) / 20.73 / 20.8

Spectral data comparison table of compound p1 with paulomenolB2,3

Position / 1H NMR of p1 / 13C NMR of paulomenol B / 13C NMR of p1
1 / ----- / 170.06 / 170.1
2 / ----- / 100.56 / 100.7
3 / ----- / 160.05 / 160.2
4 / ----- / 197.45 / 199.4
5 / 3.10, 3.20 (ABq, 20) / 48.76 / 48.9
6 / ----- / 78.94 / 79.1
7 / ----- / 188.72 / 188.8
8 / 3.88 (d, 7.5) / 78.94 / 79.1
9 / 3.52-3.44 (m) / 68.35 / 68.7
10 / 4.11-4.07 (m) / 81.07 / 81.5
11 / 3.52-3.44 (m) / 70.37 / 70.5
12 / 4.07-4.04 (m) / 75.68 / 75.9
13 / 3.76, 3.80 (ABX, 12, 7.5, 2) / 64.07 / 64.2
1’ / 5.16 (dd, 4.5, 2) / 100.19 / 100.5
2’ / 1.92, 2.27 (ABMX, 13.5, 5.5, 3) / 30.92 / 31.0
3’ / 3.66 (dd, 13, 6) / 75.08 / 75.1
3’-OMe / 3.32 (s) / 57.24 / 57.3
4’ / ----- / 74.31 / 74.3
5’ / 4.48 (q, 8) / 68.45 / 68.4
6’ / 1.29 (d, 9) / 15.92 / 16.1
7’ / 5.35 (q, 8.5) / 70.71 / 70.7
8’ / 1.28 (d, 9) / 15.93 / 17.4
1’’ / ----- / ----- / -----
2’’ / ----- / ----- / -----
3’’ / ----- / ----- / -----
4’’ / ----- / ----- / -----
5’’ / ----- / ----- / -----
1’’’ / ----- / 175.70 / 175.8
2’’’ / 2.68-2.58 (m) / 34.85 / 42.3
3’’’ / 1.22 (d, 9) / 19.39 / 27.5
4’’’ / 1.19 (d, 9) / 19.59 / 12.1
5’’’ / ----- / ----- / -----
1’’’’ / ----- / 171.19 / 171.2
2’’’’ / 2.02 (s) / 20.75 / 20.8

Spectral data comparison table of compound p3 with paulomycin E4

Position / 1H NMR of paulomycin E / 1H NMR of p3
1 / ----- / -----
2 / ----- / -----
3 / ----- / -----
4 / ----- / -----
5 / 3.15, 3.35 (AB) / 3.32-3.16 (m)
6 / ----- / -----
7 / ----- / -----
8 / 3.96 (d) / 3.96 (d, 10)
9 / 3.72 (ddd) / 3.74 (ddd, 13, 10, 2.5)
10 / 4.31 (dd) / 4.32 (dd, 2.5, 2)
11 / 4.82 (dd) / 4.83 (dd, 11, 2)
12 / 4.26 (ddd) / 4.27 (ddd, 11, 5, 2)
13 / 3.88, 3.99 (ABX) / 3.89, 4.01 (ABX, 12, 8.5, 5.0)
1’ / 5.05 (dd) / 5.05 (dd, 4, 2)
2’ / 1.88, 2.32 (ABMX) / 1.84, 2.31 (ABMX, 16, 5, 2)
3’ / 4.11 (dd) / 4.18 (dd, 11.5, 4)
3’-OMe / 3.23 (s) / 3.25 (s)
4’ / ----- / -----
5’ / 4.56 (q) / 4.55 (q, 6.5)
6’ / 0.94 (d) / 0.95 (d, 6.5)
7’ / ----- / -----
8’ / 2.24 (s) / 2.26 (s)
1’’ / ----- / -----
2’’ / ----- / -----
3’’ / 6.84 (q) / 6.83 (q, 7.0)
4’’ / 1.94 (d) / 1.96 (d, 7.0)
5’’ / ----- / -----
1’’’ / ----- / -----
2’’’ / ----- / -----
3’’’ / ----- / -----
4’’’ / ----- / -----
5’’’ / ----- / -----
1’’’’ / ----- / -----
2’’’’ / 1.98 (s) / 1.99 (s)

References

1. Argoudelis, A. D.; Brinkley, T. A.; Brodasky, T. F.; Buege, J. A.; Meyer, H. F.; Mizsak, S. A. J. Antibiot.1982, 25, 285-294.

2. Argoudelis, A. D.; Baczynskyj, L.; S. A. Mizsak, S. A.; Shilliday, F. B. J. Antibiot. 1988, 31, 1316-1330.

3. Wiley, P. F.; Mizsak, S. A.; Baczynskyj, L.;Argoudelis, A. D.; Duchamp, D. J.; Watt, W. J. Org. Chem.1986, 51, 2493-2499.

4. Argoudelis, A. D.; Baczynskyj, L.; Haak, W. J.; Knoll, W. M.; Mizsak, S. A.; Shilliday, F. B. J. Antibiot.1988, 31, 157-169.

1H and 13C spectra of compound p5 (paulomycin A)

1H and 13C spectra of compound p4 (paulomycin B)

1H and 13C spectra of compound p2 (paulomenol A)

1H and 13C spectra of compound p1 (paulomenol B)

1H spectra of compound p3 (paulomycin E)