Substitution von molekularen Klammern an den Naphthalin ...

Experimenteller Teil
13 C-NMR (126 MHz, DMSO-d6): δ [ppm] = 46.24, 46.43 (d, C-6, C-8, C-15, C-17),
63.89 (t, C-19, C-20), 118.95 (d, C-5, C-14), 120.09 (d, C-9, C-18), 124.55 (d, C-3,
C-12), 127.04 (d, C-4, C-13), 127.65 (s, C-2, C-11), 129.93 (d, C-1, C-10), 130.66
(s, C-4a, C-13a), 133.68, 133.85 (s, C-6a, C-7a, C-15a, C-16a), 139.20 (s, C-7, C-
16), 148.54 (s,C-5a, C-14a), 150.43 (s, C-8a, C-17a), 167.57 (s, CO).
HO2C 23 2
3
1
18
17
21
OH
4 5 6 7
OH
22
8 9 10
16
19 20
15
14
13
CO2H 12
meso-61d: 1 H-NMR (500 MHz, DMSO-d6): δ [ppm] = 2.25 (d, 2H, 2 J(19i-H, 19a-
H)= 7.7 Hz, 19i-H, 20i-H), 2.35 (d, 2H, 19a-H, 20a-H), 4.55 (s, 4H, H-6, H-8 H-15,
H-17),7.60 (s, 2H, H-5, H-9), 7.66 (d, 2H, H-4, H-10), 7.67 (s, 2H, H-14, H-18),
7.71 (dd, 2H, 3 J(3-H, 4-H)= 8.5Hz 4 J(3-H, 1-H)= 1.6 Hz, 3-H, 11-H), 8.25, 8.25 (s,
2H, H-1, H-13), 8.62 (d, 2H, 21-H, 22-H), 12.74 (s, 2H, COOH).
13 C-NMR (126 MHz, DMSO-d6): δ [ppm]= 46.24, 46.42 (d, C-6, C-8, C-15, C-17),
63.89 (t, C-19, C-20), 118.91 (d, C-5, C-9), 120.10 (d, C-14, C-18), 124.55 (d, C-3,
C-11), 127.06 (d, C-4, C-10), 127.62 (s, C-2, C-12), 129.93 (d, C-1, C-13), 130.66
(s, C-4a, C-9a), 133.64, 133.89 (s, C-6a, C-7a, C-15a, C-16a), 139.16, 139.23 (s,
C-7, C-16), 148.54 (s, C-5a, C-8a), 150.42 (s, C-14a, C-17a), 167.57 (s, CO).
IR (KBr): ν ~ (cm -1 ): 3441 (OH), 3049 (C-H), 2866-2991(C-H), 1720 (C=O), 1768
(C=O), 1173-1279 (C-O).
MS (70 eV), m/z (%): 639 (28) [M + ], 596 (36) [M + -COCH3], 554 (100) [M + -
2∗COCH3].
MS-ESI (377 eV): Molmasse: 526.141 ber. C34H22O6
525.1 gef. C34H22O6
11
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