I.R. Nascimento, L.M. Lopes / Phytochemistry 52 (1999) 345±350
349
3.9. (2S,3S,1'S,2'R )- and (2S,3S,1'R,2'R )-2,3-
dihydro-5-(1',2'-dihydroxypropyl)-2-(3,4-
dimethoxyphenyl)-7-methoxy-3-methylbenzofuran (O-
10A and B); 45.3, 45.5 (C-3A and B); 56.0
(6 Â OCH3), 74.2, 74.5 (C-9A and B); 78.8, 79.4 (C-8A
1
and B), 93.8 (C-2A and B). H NMR (CDCl3): d 1.24
methyl-licarinediol A+O-methyl-licarinediol B, 5)
(12H, m, H-10A and B, CH3-3A and B), 3.82 (18H, s,
6 Â OCH3), 5.08 (2H, d, J = 9.5 Hz, H-2A and B),
5.40 (2H, m, H-9A and B), 5.90 (1H, d, J = 5.9 Hz,
H-8A), 5.95 (1H, d, J = 5.2 Hz, H-8B), 6.65 to 6.53
(4H, m, H-4A and B, H-6A and B), 6.80 (2H, d,
J = 8.8 Hz, H-5'A and B), 6.92 to 6.88 (4H, m, H-2'A
and B, H-6'A and B).
Yellow oil. [a]2D5 +3.58 (CHCl3; c 1.036). (Found: C,
67.4; H, 6.9. C21H26O6 requires: C, 67.4, H, 7.0; O,
25.6%). UV lCHCl
nm (log E). 242 (3.83), 282
3
max
KBr
max
(3.68), 310 sh (3.47). IR n
cm 1: 3444, 2923, 1599,
1514, 1459, 1264, 1136, 1025. EIMS 70 eV m/z (rel.
int.): 374 [M]+ (17), 329 [M-CH3CHOH]+ (100), 165
[C6H3(OCH3)(OCH3)CO]+
(26),
151
1
[C7H5(OCH3)(OCH3)]+ (34). H and 13C NMR spec-
tra see Tables 1 and 2.
Acknowledgements
3.10. (2S,3S )-2,3-dihydro-2-(3,4-dimethoxyphenyl)-7-
methoxy-3-methyl-5-(2-oxopropyl)benzofuran
(licarinone, 5a)
The authors thank the Fundacao de Amparo a
Pesquisa do Estado de Sao Paulo for ®nancial support,
including the fellowship to I. R. Nascimento; Dr
Massayoshi Yoshida and Dr Shirley Schreier (IQ-USP,
Sao Paulo) for measurements of CD.
Yellow oil. [a ]2D5
36.38 (CHCl3; c 0.880). CD
(CH3OH, c 0.1) [y ]228 10,324, [y ]242 0, [y]255 +3204.
IR n cm 1: 2930, 2849, 1720, 1604, 1508, 1264, 1154.
1H NMR (CDCl3): d 1.31 (3H, d, J = 6.8 Hz, CH3-3),
2.12 (3H, s, H-10), 3.40 (1H, m, H-3), 3.59 (2H, s, H-
8), 3.81 (9H, s, 3 Â OCH3), 5.05 (1H, d, J = 9.6 Hz,
H-2), 6.55 (2H, brs, H-4 and H-6), 6.77 (1H, d,
J = 8.1 Hz, H-5'), 6.92 to 6.88 (2H, m, H-2' and H-
6').
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