was extracted with four 50-ml ethyl acetate portions. The combined organic phases were dried over anhydrous
sodium sulfate and evaporated to dryness in vacuum. The residue was initially purified by passing through a
silica gel column using 1:10 methylene chloride–petroleum ether as the eluent. The yellow oily residue was
separated by chromatography on a silica gel column (5/40 fraction) using petroleum ether as the eluent.
The major diastereomer of compound 4 was obtained as a white powder; mp 169–170°C (petroleum
1
ether). The yield was 1.39 g (36%). H NMR spectrum, , ppm (J, Hz): 2.19 (3H, s, CH3); 2.24 (3H, s, CH3");
2.32 (3H, s, CH3'); 5.18 (1H, d, J = 4.2, H-9); 5.26 (1H, d, J = 4.2, H-4); 5.87 (1H, d, J = 3.0, H-4"); 5.88 (1H, s,
H-3); 5.94 (1H, d, J = 3.0, H-3"); 7.02 (2H, m, AA'BB' system, H-2', H-6'); 7.08 (1H, d, J = 2.3, H-8); 7.11 (2H,
m, AA'BB' system, H-3', H-5'); 7.12 (1H, dd, J = 2.3, J = 8.4, H-6); 7.29 (1H, d, J = 8.4, H-5). 13C NMR
spectrum, , ppm: 13.6 (CH3"); 13.7 (CH3); 21.1 (CH3'); 38.1 (C-4); 44.2 (C-9); 105.4 (C-3); 106.0 (C-4"); 107.2
(C-3"); 117.2 (C-3a); 126.7 (C-6); 128.4 (C-2', C-6'); 129.5 (C-3', C-5'); 130.0 (C-8); 130.7 (C-5); 132.4 (C-7);
133.6 (C-4a); 136.5 (C-4'); 139.5 (C-8a); 140.1 (C-1'); 147.9 (C-9a); 151.5 (C-5"); 151.9 (C-2); 154.9 (C-2").
Mass spectrum, m/z (Irel, %): 390/388 [M]+ (23/62), 347/345 (21/60), 308/306 (35/100), 296 (34), 253 (16), 219
(15), 101 (15), 59 (45), 43 (53). Found, %: C 77.35; H 5.49. C25H21ClO2. Calculated, %: C 77.21; H 5.44.
The minor diastereomer of compound 4 was obtained as a white powder; mp 146–147°C (petroleum
1
ether). The yield was 0.74 g (19%). H NMR spectrum, , ppm (J, Hz): 2.22 (3H, s, CH3); 2.27 (3H, s, CH3");
2.32 (3H, s, CH3'); 5.11 (1H, d, J = 4.0, H-9); 5.16 (1H, d, J = 3.0, H-4); 5.87 (1H, d, J = 3.0, H-4"); 5.90 (1H, d,
J = 3.0, H-3"); 5.95 (1H, s, H-3); 7.10 (2H, m, AA'BB' system, H-3', H-5'); 7.14 (1H, d, J = 2.3, H-8); 7.16 (1H,
dd, J = 2.3, J = 8.3, H-6); 7.17 (2H, m, AA'BB' system, H-2', H-6'); 7.40 (1H, d, J = 8.3, H-5). 13C NMR
spectrum, , ppm: 13.6 (CH3"); 13.7 (CH3); 21.0 (CH3'); 38.3 (C-4); 44.4 (C-9); 105.5 (C-3); 106.0 (C-4"); 106.6
(C-3"); 116.7 (C-3a); 126.7 (C-6); 128.5 (C-2', C-6'); 129.3 (C-3', C-5'); 130.0 (C-8); 131.2 (C-5); 132.4 (C-7);
133.4 (C-4a); 136.4 (C-4'); 139.5 (C-8a); 140.2 (C-1'); 148.2 (C-9a); 151.4 (C-5"); 152.0 (C-2); 155.3 (C-2").
Mass spectrum, m/z (Irel, %): 390/388 [M]+ (36/100), 347/345 (28/83), 308 (44), 253 (37), 218 (23), 119 (15), 59
(27), 43 (72). Found, %: C 77.13; H 5.47. C25H21ClO2. Calculated, %: C 77.21; H 5.44.
This work was carried out in the framework of the Federal Program for Scientific and Science Teaching
Personnel for Innovation in Russia for 2009-2013 (endeavor 1.3.1, State Contract No. P2347) with the support
of the Council for Grants of the Russian Federation President (Grant MK-4902.2010.3).
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