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Cbz
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H
O
H
O
186b
3a,6-Dimethyl-1,7,9-trioxo-8-phenyl-3,3a,5,6,6a,7,8,9,9a,9b,10,11,11a,11b-tetradecahydro-
H
1H-2-oxa-4,8-diazacyclopenta[a]pyrene-4-carboxylic acid benzyl ester (186b). Prepared by
following general procedure L, using 185 (10 mg, 27 µmol), N-phenylmaleimide (7 mg, 40
µmol). Reaction time (6 h at rt). Isolated yield 186b (15 mg, >95%). 1 H NMR (300 MHz,
CDCl3): δ 7.44-7.33 (m, 8H), 7.14-7.09 (m, 2H), 5.31 (d, J = 11.8 Hz, 1H), 5.13 (s, 2H), 4.44 (d,
J = 18.1 Hz, 1H), 4.13 (d, J = 11.8 Hz, 1H), 3.67 (dq, J = 18.1, 2.2 Hz, 1H), 3.30 (dd, J = 8.5, 6.3
Hz, 1H), 3.19 (dd, J = 8.5, 5.2 Hz, 1H), 3.13-3.04 (m, 1H), 2.69-2.61 (m, 2H), 2.45 (bs, 1H),
2.30-2.17 (m, 1H), 2.13-1.90 (m, 2H), 1.54 (d, J = 7.3 Hz, 3H), 1.40 (s, 3H); 13 C NMR (75 MHz,
CDCl3): δ 176.4, 176.2, 173.8, 155.9, 136.2, 132.1, 131.5, 129.1, 128.6, 128.6, 128.1, 127.7,
127.4, 126.1, 71.1, 67.3, 56.1, 46.4, 44.4, 42.1, 41.6, 36.9, 33.0, 23.3, 21.8, 20.7, 12.9, 1.0; IR
(thin film): ν 2940, 1747, 1706, 1381 cm -1 ; MS m/z (%) 540 (8), 495 (37), 449 (29), 405 (65), 91
(100); EI-HRMS calcd for C32H32N2O6 m/z [M] + 540.2260; found 540.2281.
Cbz
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186c
3a,6-Dimethyl-1,7,9-trioxo-3,3a,6,6a,7,9,9a,9b,10,11,11a,11b-dodecahydro-1H,5H-2,8-
dioxa-4-azacyclopenta[a]pyrene-4-carboxylic acid benzyl ester (186c). Prepared by following
general procedure L, using 185 (18 mg, 49 µmol), maleic anhydride (7 mg, 71 µmol). Reaction
time (3 h at rt). Isolated yield 186c (18 mg, 78%).
1 H NMR (300 MHz, CDCl3): δ 7.40-7.33 (m, 5H), 5.22 (d, J = 11.9 Hz, 1H), 5.13 (s, 2H), 4.37
H
230
O
O
N
O
O
O
Ph