7236
E. Caballero et al. / Tetrahedron Letters 42 (2001) 7233–7236
H
N
N
a) Acetone
r.t. 48h
O
O
O
N
O
O
O
H
H
b) c. HCl
CH2Cl2
N
H
N
N
O
N
TBDMSO
H
9 (51%)
1
Arcyriaflavin A
p-MeO-PhNHNH2
AcOH - EtOH
reflux, 2h
N
O
O
N
O
O
H
H
DDQ
MeO
MeO
Toluene, 3h
N
N
H
N
N
H
Grooved analogue 26 (65%)
25 (58%)
Scheme 2. Synthesis of a grooved analogue of arcyriaflavin A.
8. Adeva, M.; Buono, F.; Caballero, E.; Medarde, M.; Tome´,
F. Synlett 2000, 832–834.
References
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the dark, for two days. Due to the low stability of the
dienes, they were prepared and immediately reacted with
the dienophiles.
14. All the analytical data for the synthesized compounds are
consistent with their structure, as for instance: compound
25, orange oil (58%). 1H NMR (200 MHz, CDCl3): l 2.63
(s, 3H), 3.07 (m, 2H), 3.6–3.9 (m, 2H), 3.70 (s, 3H), 3.93
(s, 3H), 4.35 (d, J=7.4 Hz, 1H), 6.86 (dd, J=8.4, 2.6, 1H),
6.99 (s, 1H), 7.20 (m, 3H), 7.22 (d, J=8.4 Hz, 1H), 7.43
(s, 1H), 7.60 (d, J=8.2 Hz, 1H), 7.95 (s, 1H). 13C NMR
(50 MHz, CDCl3): l 24.3, 27.7, 31.4, 32.8, 41.2, 45.2, 55.9,
101.9, 104.1, 109.4, 111.5, 112.3, 113.6, 118.5, 119.1, 121.8,
127.3, 127.8, 130.8, 135.4, 136.5, 154.6, 176.7, 177.8.
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Medarde, M.; Sahagu´n, H.; Tome´, F. Bioorg. Med. Chem.
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3387–3394.
1
Compound 26, red powder (65%). H NMR (400 MHz,
Pyr-d5): l 3.21 (s, 3H), 3.65 (s, 3H), 4.00 (s, 3H), 7.27 (dd,
J=8.0, 8.0, 1H), 7.37 (dd, J=8.0, 8.0, 1H), 7.41 (d, J=8.0,
1H), 7.43 (dd, J=8.6, 2.6, 1H), 7.70 (d, J=8.8, 1H), 7.95
(s, 1H), 8.01 (d, J=8.0, 1H), 8.15 (s, 1H), 9.17 (d, J=2.4,
1H), HRMS: calcd for C25H19N3O3 [M+]: 409.1426; found:
409.1655. Anal. calcd for C25H19N3O3: C, 73.34; H, 4.68;
N, 10.26; O, 11.72%; found: C, 73.30; H, 4.72; N, 10.22%.