N.R. Guz, F.R. Stermitz / Phytochemistry 54 (2000) 897±899
899
vacuo gave pure epoxides as clear oils in excellent
yield (>95%). The diacetate coniferyl epoxides rapidly
degraded when not stored in solution (CHCl for our
MHz, CDCl ): d 54.17 (CH), 55.95 (OCH ), 71.67
3
3
(CH ), 85.87 (CH), 108.58 (CH), 114.26 (CH), 118.96
(CH), 132.94 (C), 145.24 (C), 146.69 (C); EIMS (direct
probe, m/z rel. int.): 358(70), 327(11), 235(15), 205(30),
2
3
experiments).
1
63(38), 151(100), 137(72).
3.2. cis-Epoxyconiferyl alcohol diacetate
1
H NMR spectral data (300 MHz, CDCl ): d 2.08
3
Acknowledgements
(
s, 3H, CH ) 2.32 (s, 3H, CH ), 3.47 (m, 1H, CH),
3 3
3.85 (s, 3H, OCH ), 3.87 (m, 1H, CH), 4.09 (dd, 2H, J
=
3
This research was supported by grant CHE-9619213
from the National Science Foundation. Mass spectra
were obtained on an instrument supported by National
Institutes of Health grant GM49631.
12.0, 4.0 Hz, CH ), 4.17, (d, 1H, J = 4.0 Hz, CH),
2
6
2
.92 (d, 1H, J = 2.0 Hz, CH), 6.95 (dd, 1H, J = 12.0,
.0 Hz, CH), 7.03 (d, 1H, J = 8.0 Hz, CH); C NMR
13
spectral data (75 MHz, CDCl ): d 20.55 (CH ), 20.65
3
3
(
(
(
(
CH ), 55.85 (OCH ), 55.91 (CH), 56.12 (CH), 62.22
CH ), 110.09 (CH), 118.37 (CH), 122.72 (CH), 132.94
3 3
2
C), 139.33 (C), 151.01 (CH), 168.83 (C1O), 170.65,
References
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C1O); HR-FABMS (MH ): calculated: 281.1020;
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3
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3
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(
(
(
(
CH ), 20.70 (CH ), 55.83 (OCH ), 56.19 (CH), 59.31
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3
3
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2
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3
.4. (2) Pinoresinol
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1
H NMR spectral data (400 MHz, CDCl ): d 3.10
3
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(
(
(
m, 2H, CH), 3.88 (dd, 2H, CH, J = 9.2, 3.2 Hz), 3.91
s, 6H, OCH ), 4.25 (dd, 2H, CH, J = 9.0, 6.8), 4.74
d, 2H, CH, J = 4.4 Hz), 5.59 (bs, 2H, OH), 6.82 (dd,
3
6136.
2
6
H, CH, J = 8.0, 2.0), 6.88 (d, 2H, CH, J = 8.0),
.90 (d, 2H, J = 1.6), C NMR spectral data (100
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13