ORDER
REPRINTS
638
Lantan˜o et al.
125.2, 126.5, 126.6, 126.8, 128.2, 128.7, 136.7, 137.9, 142.5, 143.9, 145.4,
148.9. Diastereomer 19a. dH 2.57 (1H, dd, J: 9.2 and 16.7, CH2), 2.67 (1H, dd,
J: 7.9 and 16.7, CH2), 3.75 (1H, m, overlaps with OCH3, CH2CH), 3.81 (3H, s,
OCH3), 3.95 (3H, s, OCH3), 4.69 (1H, d, J: 7.9, ArCHAr), 4.78 (1H, d, J:
7.9 Hz, ArCHAr), 6.72 (1H, s, Ar), 6.97 (1H, s, Ar), 7.01–7.55 (9H, m, Ar); dC
34.1, 50.0, 53.2, 55.6, 56.1, 107.3, 108.7, 123.7, 124.6, 126.4, 126.5, 128.2,
129.2, 135.7, 136.4, 141.9, 143.5, 145.0, 148.7, 148.9.
(4bR/S,9S/R,9aS/R)-7-Methoxy-9-phenyl-10,11,4b,9a-tetrahydro-
benzo[c]fluoren-6-ol (20a) and (4bR/S,9R/S,9aS/R)-7-methoxy-9-
phenyl-10,11,4b,9a-tetrahydrobenzo[c]fluoren-6-ol (20b). General pro-
cedure was carried out with alcohol 1 (0.13 g, 0.58 mmol), dihydronaphtalene
16 (0.12 g, 0.92 mmol) and SnCl4 (0.19 g, 0.75 mmol). p-Tlc (80 : 20 hexane:
ethyl acetate) afforded 0.08 g (41%) of 20a and 20b as a 1.6 : 1 (20a/20b)
(clear oil). Found: C, 84.3; H, 6.6. C24H22O2. Calcd: C, 84.2; H, 6.5. Mayor
diastereomer 20a. dH 1.79 (1H, m, CHCH2CH2), 1.95 (1H, m, CHCH2CH2),
2.80 (3H, m, CHArCHCH2, CHCH2Ar), 3.75 (3H, s, OCH3), 4.12 (1H, d, J:
5.7, ArCHAr), 4.41 (1H, d, J: 7.5, ArCHAr), 5.55 (1H, s, OH), 6.52 (1H, s,
Ar), 7.03 (1H, s, Ar), 7.10–7.45 (9H, m, Ar); dC 25.9, 27.6, 45.9, 49.5, 55.7,
56.0, 107.8, 110.8, 125.8, 126.0, 126.3, 128.0, 128.5, 128.7, 129.3, 136.2,
137.1, 137.4, 138.6, 144.7, 144.8, 145.9. Minor diastereomer 20b dH 1.1 (1H,
m, CHCH2CH2), 1.3 (1H, m, CHCH2CH2), 2.60 (2H, m, CHCH2CH2Ar),
2.80 (1H, m, CHArCHCH2), 3.79 (3H, s, OCH3), 4.31 (1H, d, J: 5.7 Hz,
ArCHAr), 4.63 (1H, d, J: 6.1, ArCHAr), 5.53 (1H, s, OH), 6.69 (1H, s, Ar),
6.90 (1H, s, Ar), 7.08 (1H, d, J: 7.5 Hz, Ar), 7.18 (1H, d, J: 7.2, Ar), 7.26–7.46
(7H, m, Ar); dC 21.3, 28.9, 46.7, 47.3, 54.5, 56.3, 108.1, 110.5, 125.7, 126.1,
126.6, 128.2, 128.9, 129.7, 130.1, 134.0, 136.3, 137.2, 139.1, 140.0, 144.5,
145.3.
(4bR/S,9S/R,9aS/R)-6,7-dimethoxy-9-phenyl-10,11,4b,9a-tetrahy-
drobenzo[c]fluorene (21a) and (4bR/S,9R/S,9aS/R)-6,7-dimethoxy-9-
phenyl-10,11,4b,9a-tetrahydrobenzo[c]fluorene (21b). General procedure
was carried out with alcohol 2 (0.14 g, 0.58 mmol), dihydronaphtalene 16
(0.12 g, 0.92 mmol) and SnCl4 (0.19 g, 0.75 mmol). p-Tlc (80 : 20 hexa-
ne : ethyl acetate) afforded 0.10 g (54%) of 21a and 21b as a 1.5 : 1 (21a/21b)
(clear oil). m/z (EI) 356.1884 (Mþ, 356 C25H24O2) requires 356.1776, 356
(100), 227 (17) and 91 (13%). Mayor diastereomer 21a dH 1.79 (1H, m, J: 4.9,
5.1 and 13.3, CHCH2CH2Ar), 1.95 (1H, m, J: 4.9, 5.1, 7.9 and 13.3,
CHCH2CH2Ar), 2.80 (3H, m, J: 5.1, 7.4 and 7.9, CHArCHCH2, CH2Ar), 3.73
(3H, s, OCH3), 3.87 (3H, s, OCH3), 4.13 (1H, d, J: 5.4, ArCHAr), 4.42 (1H, d,
J: 7.4, ArCHAr), 6.54 (1H, s, Ar), 6.94 (1H, s, Ar), 7.11–7.33 (8H, m, Ar),
7.42 (1H, d, J: 7.7, Ar); dC 26.2, 27.8, 46.3, 49.5, 55.9, 56.0, 56.1, 108.1 108.6,
125.9, 126.0, 126.3, 127.9, 128.5, 128.9, 129.0, 136.5, 136.8, 137.4, 137.6,
137.8, 148.4, 148.5. Minor diastereomer 21b dH 1.09 (1H, dd, J: 3.6 and 13.1,