Zinc-mediated cyclodimerization of 1,5-diaryl-1,4-pentadien-3-one in aqueous solution under ultrasound irradiation

Article abstract of DOI:10.1080/00397911.2010.531440

Synthesis of 2-cinnamoyl-1-styryl-3,4-diarylcyclopentanol via cyclodimerization of 1,5-diaryl-1,4-pentadien-3-one mediated by zinc was carried out in good yields at room temperature in NH₄Cl (aq.) and tetrahydrofuran under ultrasonic irradiatio

Full text of DOI:10.1080/00397911.2010.531440

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Zinc-Mediated Cyclodimerization of 1,5-
Diaryl-1,4-pentadien-3-one in Aqueous
Solution Under Ultrasound Irradiation
Ji-Tai Li a , Chao Du a & Xin-Li Zhai a
a Key Laboratory of Analytical Science and Technology of Hebei
Province, Key Laboratory of Medical Chemistry and Molecular
Diagnosis, Ministry of Education, College of Chemistry and
Environmental Science, Hebei University, Baoding, China
Accepted author version posted online: 24 Aug 2011.Published
online: 11 Nov 2011.
To cite this article: Ji-Tai Li , Chao Du & Xin-Li Zhai (2012) Zinc-Mediated Cyclodimerization
of 1,5-Diaryl-1,4-pentadien-3-one in Aqueous Solution Under Ultrasound Irradiation, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry,
42:6, 820-827, DOI: 10.1080/00397911.2010.531440
To link to this article: http://dx.doi.org/10.1080/00397911.2010.531440
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Synthetic Communications1, 42: 820–827, 2012
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397911.2010.531440
ZINC-MEDIATED CYCLODIMERIZATION OF
1,5-DIARYL-1,4-PENTADIEN-3-ONE IN AQUEOUS
SOLUTION UNDER ULTRASOUND IRRADIATION
Ji-Tai Li, Chao Du, and Xin-Li Zhai
Key Laboratory of Analytical Science and Technology of Hebei Province,
Key Laboratory of Medical Chemistry and Molecular Diagnosis, Ministry
of Education, College of Chemistry and Environmental Science,
Hebei University, Baoding, China
GRAPHICAL ABSTRACT
Abstract Synthesis of 2-cinnamoyl-1-styryl-3,4-diarylcyclopentanol via cyclodimerization
of 1,5-diaryl-1,4-pentadien-3-one mediated by zinc was carried out in good yields at room
temperature in NH4Cl (aq.) and tetrahydrofuran under ultrasonic irradiation. In compari-
son with conventional methods, the main advantages of the present procedure are shorter
reaction time and better yields.
Keywords 2-Cinnamoyl-1-styryl-3-4-diarylcyclopentanol; cyclodimerization; synthesis;
ultrasound irradiation
INTRODUCTION
Carbon–carbon bond formation is the backbone of organic synthesis, and the
reductive dimerization of carbonyl compounds by active metals is valuable for form-
ing carbon–carbon bonds. Kapoor et al.[1] reported the reductive cyclodimerization
of a,b-unsaturated ketones at room temperature in dimethylformamide (DMF) for
3 h using zinc powder in the presence of a catalytic amount of HgCl2 to initiate
the single-electron transfer (SET)[2] and give 2-cinnamoyl-1-styryl-3,4-diphenyl-
cyclopentanol in 55% yield. A similar type of reaction was also performed using
catalysts, such as Sm,[3] SmI2,[4,5] Zn-TiCl4,[6] Yb,[7] tributyltin hydride,[8] and
NdCl3–lithium naphthalide.[9] Cabrera et al. reported that the cyclodimerization of
Received May 6, 2010.
Address correspondence to Ji-Tai Li, College of Chemistry and Environmental Science, Hebei
University, Wusi East Road No. 180, Baoding 071002, China. E-mail: lijitai@hbu.cn
820

2-CINNAMOYL-1-STYRYL-3,4-DIARYLCYCLOPENTANOL
821
1,5-diphenyl-1,4-pentadien-3-one catalyzed by SmI2 gave 2-cinnamoyl-1-styryl-
3,4-diphenylcyclopentanol in 40% yield in the presence of hexamethylphosphora-
mide–tetrahydrofuran (HMPA-THF) for 5 min.[4] Kumar et al. reported that the
synthesis of 2-cinnamoyl-1-styryl-3,4-diphenylcyclopentanol was carried out in
68% yield under stirring via the cyclodimerization of bischalcone catalyzed by Zn
powder in a mixture of aqueous NH4Cl and THF at room temperature for 5 h.[10]
However, in spite of their potential utility, some of the reported methods suffer from
drawbacks such as longer reaction times and lower yields. In addition, the cyclodi-
merization of bischalcone-bridging substituent in the benzene ring has not been
involved in literature.
Ultrasound has increasingly been used in organic synthesis in the last three
decades. The effects of ultrasound observed during organic reactions are due to cavi-
tation, a physical process that creates, enlarges, and implodes gaseous and vaporous
cavities in an irradiated liquid. Cavitation induces very high local temperatures and
pressures inside the bubbles (cavities), leading to turbulent flow of the liquid and
enhanced mass transfer.[11] A large number of organic reactions can be carried out
with better yields, shorter reaction times, and milder conditions under ultrasonic
irradiation. Earlier data clearly show that ultrasonic irradiation can activate the sur-
face of metal powder, reduce the particle size, and bring about an effective surface
modification. Many metal-involved organic reactions have been accelerated under
ultrasound.[12]
Herein, we report the synthesis of 2-cinnamoyl-1-styryl-3,4-diarylcyclopenta-
nol from 1,5-diaryl-1,4-pentadien-3-one and zinc powder in NH4Cl-THF aqueous
solution under ultrasonic irradiation (Scheme 1).
RESULTS AND DISCUSSION
The results are summarized in Table 1. It can be easily seen that the cyclodi-
merization of 1,5-diaryl-1,4-pentadien-3-one using zinc in aqueous solution was car-
ried out in good yield under ultrasonic irradiation. We observed the effect of
ultrasonic irradiation on the reaction. Under 25-kHz irradiation for 0.5 h, the cyclo-
dimerization of 1,5-diphenyl-1,4-pentadien-3-one gave the desired product in 96%
yield (Table 1, entry 1). While under 40-kHz irradiation, 2-cinnamoyl-1-styryl-
3,4-diphenylcyclopentanol was obtained in 89% yield within the same time
(Table 1, entry 2). It is shown that lower frequency of ultrasonic irradiation
improved the yield. We also did the experiments in the absence of ultrasound, and
the cyclodimerization of 1,5-diphenyl-1,4-pentadien-3-one was carried out in 40%
Scheme 1. Synthesis of 2-cinnamoyl-1-styryl-3,4-diarylcyclopentanol.

822
J.-T. LI, C. DU, AND X.-L. ZHAI
Table 1. Effect of reaction conditions on the yield of 2-cinnamoyl-1-styryl-3,4-diphenylcyclopentanol (2a)
under ultrasonic irradiationa
Entry
Amount of Zn (mmol)
Amount of NH4Cl (mmol)
Frequency (kHz)
Isolated yield (%)
1
2
3
4
5
6
7
8
2.0
2.0
2.2
1.75
1.5
2.0
2.0
2.0
2.0
2.0
2.0
2.0
2.0
1.0
1.5
2.0
25
40
25
25
25
25
25
stir
96
89
87
89
85
83
91
40
aSubstrate: 1,5-diphenyl-1,4-pentadien-3-one, 1 mmol; H2O, 1 mL; THF, 4 mL; 30 ꢀC; irradiation time,
0.5 h.
yield (Table 1, entry 8) using stirring for 0.5 h at the same conditions. It is apparent
that the cyclodimerization can be finished in a shorter reaction time to give better
yield under ultrasonic irradiation.
The effect of amount of Zn powder and NH4Cl on the reaction under ultrasonic
irradiation was shown in Table 1. When the amount of NH4Cl was 2.0 equivalents, the
yield increased from 85% (Table 1, entry 5) to 96% (Table 1, entry 1) when Zn powder
was increased from 1.5 to 2.0 equivalents within the same time. Further increase of the
amount of Zn had no effect on the yield of 2-cinnamoyl-1-styryl-3,4-diphenylcyclo-
pentanol. The results showed that changing the amount of Zn had a significant effect
on the yield, and the optimum amount was 2.0 equivalents. When the amounts of
NH4Cl were 1.0, 1.5, and 2.0 equivalents, the yields of 2a were 83% (Table 1, entry
6), 91% (Table 1, entry 7), and 96% (Table 1, Entry 1) respectively.
From these results, the following conditions were chosen: 1,5-diphenyl-1,4-
pentadien-3-one (1 mmol), Zn (2.0 mmol), NH4Cl (2.0 mmol), H2O (1 mL), and
THF (4 mL). Using this reaction system, we did a series of experiments for synthesis
of 2-cinnamoyl-1-styryl-3,4-diarylcyclopentanol under 25-kHz ultrasonic irradiation.
The results are summarized in Table 2.
As shown in Table 2, cyclodimerization of 1,5-diaryl-1,4-pentadien-3-one was
carried out in good yields in a mixture of aqueous ammonium chloride and THF at
room temperature under ultrasonic irradiation. According to the method reported in
the literature,[10] the reaction time was 5 h and the yield of 2a was 68%, whereas
under ultrasonication, compound 2a was obtained in 96% (Table 2, entry a). Under
stirring alone without ultrasound, 2c and 2d were obtained in 10% (Table 2, entry c),
and 7% (Table 2, entry d) yield for 13 h respectively with the other reaction con-
ditions consistent, whereas under ultrasonic irradiation, the yields of 2c and 2d were
95% for 2 h and 65% for 1 h, respectively. It is apparent that the ultrasound can
accelerate the reaction significantly.
In the present procedure, bischalcones carrying electron-donating groups in the
benzene rings and 1,5-diphenyl-1,4-pentadien-3-one gave good results. For example,
the yields of 2a, 2b, and 2c were 96%, 91%, and 95%, whereas bischalcones carrying
electron-withdrawing groups gave yields of 2d, 2e, and 2f as 65%, 51%, and 73%
respectively. It indicates that present method has some limitations with respect to
bischalcones carrying electron-withdrawing groups.

2-CINNAMOYL-1-STYRYL-3,4-DIARYLCYCLOPENTANOL
823
Table 2. Synthesis of 2-cinnamoyl-1-styryl-3,4-diarylcyclopentanol under ultrasound irradiation
Isolated yield (%) (stir)
Entry
Ar1
C6H5
Ar2
C6H5
Time (h) (stir)a
2
3
a
b
c
d
e
f
0.5
96
91
—
—
p-CH3C6H4
p-CH3OC6H4
p-ClC6H4
p-CH3C6H4
p-CH3OC6H4
p-ClC6H4
m-ClC6H4
o-ClC6H4
C6H5
1
2 (13)
1 (13)
95 (10)
65 (7)
51
—
31 (17)
41
21
m-ClC6H4
o-ClC6H4
p-ClC6H4
1
1
1
2
2
73
51
g
h
i
27
—
p-CH3C6H4
p-CH3OC6H4
C6H5
C6H5
64
97
—
aStirring alone without ultrasound.
The relative stereochemistry of the products was assigned by nuclear Overhau-
ser effect spectroscopy (NOESY) study. In the NOESY experiment of compound 2a,
nuclear Overhauser effects (NOE) between H2 and H4, between H4 and H5b,
between H5b and H2, between H3 and the hydrogen atom of the OH group, and
between H5a and the hydrogen atom of the OH group were observed. As shown
in Fig. 1, the experiment indicates the cis-position of C5-Hb with C4-H, and
C5-Ha with the hydrogen atom of the OH group. These observations show that
the relative stereochemistry in compound 2a is 1,2-cis, 2,3-trans, and 3,4-trans.
In conclusion, an efficient synthesis of some 2-cinnamoyl-1-styryl-3,4-diarylcy-
clopentanol from 1,5-diaryl-1,4-pentadien-3-one has been developed under ultra-
sonic irradiation. Compared with the conventional method, this method provided
several advantages such as shorter reaction time and better yield.
EXPERIMENTAL
Apparatus and Analysis
1,5-Diaryl-1,4-pentadien-3-ones were prepared according to the literature.[13]
Zn powder was activated with 5% HCl solution. Melting points were uncorrected.
Figure 1. Observed NOE interactions for 2a.

824
J.-T. LI, C. DU, AND X.-L. ZHAI
The 1H NMR and 13C NMR spectra were recorded on a Bruker Avance 600
(600-MHz) spectrometer using tetramethylsilane (TMS) as internal standard and
CDCl3 as solvent. Mass spectra were determined on a Agilent Technologies 6310
Lon Trap LC=MS (ESI). Sonication was performed in Shanghai Branson
BUG25-06 (or 40-06) ultrasonic cleaner (with a frequency of 25 or 40-kHz and a
nominal power 250 W). The reaction flasks were immersed in every place of the clea-
ner in such way that the surface of reactants was slightly lower than the water in the
cleaner.
General Procedure
A 50-mL round flask was charged with 1,5-diaryl-1,4-pentadien-3-one (1,
1 mmol), zinc powder (2.0 mmol), NH4Cl (2.0 mmol), H2O (1 mL), and THF
(4 mL) in one portion. The mixture was irradiated in the ultrasonic cleaning bath
at 30 ꢀC for the period of time as indicated in Table 2 (the reaction was followed
by thin-layer chromatography, TLC). After the completion of the reaction, the
resulting suspension was filtered to remove the Zn powder and washed with dichlor-
omethane. The filtrate was separated, and the dichloromethane layer was washed
with water (3 ꢁ 5 mL) and dried over sodium sulfate. The solvent was removed under
reduced pressure. The crude product was purified by column chromatography on sil-
ica gel (200–300 mesh) eluted with petroleum ether or a mixture of petroleum ether
and ethyl acetate (10:1–5:1) to afford the product. The authenticity of compound 2a
1
was established by comparing its melting point and H NMR and 13C NMR data
1
with those reported in the literature.[11] The rest were established by H NMR,
13C NMR, and mass spectrometry (MS).
Compound 2a
1
White solid, mp 219–221 ꢀC; H NMR: dH 2.33 (dd, J ¼ 14.6, 5.6 Hz, 1H, H5),
2.74 (dd, J ¼ 14.6, 11.3 Hz, 1H, H5), 3.60–3.64 (m, 1H, H4), 3.69 (d, J ¼ 12.1 Hz, 1H,
H2), 3.90 (dd, J ¼ 10.0, 12.1 Hz, 1H, H3), 5.07 (s, 1H, OH), 6.26 (d, J ¼ 16.1 Hz, 1H,
H
vinyl), 6.45 (d, J ¼ 15.8 Hz, 1H, Hvinyl), 6.85 (d, J ¼ 15.8 Hz, 1H, Hvinyl), 7.16–7.37
(m, 21H, Ph-H, Hvinyl); 13C NMR: dC 203.1 (C O), 144.0, 143.9, 140.5, 136.7,
134.0, 133.8, 130.7, 128.6, 127.8, 127.4, 127.0, 126.7, 126.6, 126.5, 126.3, 82.8,
65.2, 59.0, 51.6, 48.4 ppm; m=z (ESI): calcd. for C34H30O2 [M þ Na]þ 493.
=
Compound 2b
White solid, mp 190–192 ꢀC; 1H NMR: dH 2.27–2.35 (m, 13H, H5, 4CH3), 2.70
(dd, J ¼ 14.4, 11.4 Hz, 1H, H5), 3.54–3.56 (m, 1H, H4), 3.62 (d, J ¼ 12.0 Hz, 1H, H2),
3.83 (dd, J ¼ 10.2, 12.0 Hz, 1H, H3), 5.11 (s, 1H, OH), 6.26 (d, J ¼ 16.2 Hz, 1H,
H
vinyl), 6.38 (d, J ¼ 15.6 Hz, 1H, Hvinyl), 6.79 (d, J ¼ 15.6 Hz, 1H, Hvinyl), 7.05–7.30
(m, 17H, Ph-H, Hvinyl); 13C NMR: dC 203.2 (C O), 143.8, 141.3, 141.2, 137.7,
137.2, 136.4, 135.6, 134.0, 133.0, 131.5, 129.5, 129.3, 129.2, 129.0, 128.5, 128.3,
127.8, 127.7, 126.5, 125.9, 82.7, 65.4, 58.6, 51.0, 48.5, 21.5, 21.1, 21.0, 20.9 ppm;
m=z (ESI): calcd for C38H38O2 [M þ Na]þ 549.
=

2-CINNAMOYL-1-STYRYL-3,4-DIARYLCYCLOPENTANOL
825
Compound 2c
White solid, mp 162–164 ꢀC; 1H NMR: dH 2.22 (dd, J ¼ 15.0, 6.0 Hz, 1H, H5),
2.66 (dd, J ¼ 14.6, 12.0 Hz, 1H, H5), 3.45–3.49 (m, 1H, H4), 3.56 (d, J ¼ 12.0 Hz, 1H,
H2), 3.67–3.79 (m, 13H, 4OCH3, H3), 5.14 (s, 1H, OH), 6.14 (d, J ¼ 15.6 Hz, 1H,
H
vinyl), 6.25 (d, J ¼ 16.2 Hz, 1H, Hvinyl), 6.60 (d, J ¼ 16.2 Hz, 1H, Hvinyl), 6.76–7.31
(m, 17H, Ph-H, Hvinyl); 13C NMR: dC 203.3 (C O), 161.8, 159.1, 158.4, 158.0, 143.7,
136.4, 132.8, 131.8, 130.4, 129.6, 128.8, 127.7, 124.6, 114.2, 114.0, 113.9, 113.7, 82.7,
65.2, 58.6, 55.3, 50.9, 48.5 ppm; m=z (ESI): calcd. for C38H38O6 [M þ Na]þ 613.
=
Compound 2d
1
White solid, mp 180–181 ꢀC; H NMR: dH 2.25 (dd, J ¼ 15.0, 5.4 Hz, 1H, H5),
2.71 (dd, J ¼ 14.6, 11.3 Hz, 1H, H5), 3.48–3.52 (m, 1H, H4), 3.58 (d, J ¼ 12.6 Hz, 1H,
H2), 3.79 (dd, J ¼ 10.2, 12.0 Hz, 1H, H3), 4.92 (s, 1H, OH), 6.19 (d, J ¼ 16.2 Hz, 1H,
H
vinyl), 6.37 (d, J ¼ 15.6 Hz, 1H, Hvinyl), 6.78 (d, J ¼ 15.6 Hz, 1H, Hvinyl), 7.16–7.33
(m, 17H, Ph-H, Hvinyl); 13C NMR: dC 201.9 (C O), 142.8, 142.1, 138.7, 137.1
134.9, 133.8, 133.3, 133.0, 132.3, 129.6, 129.3, 129.1, 129.0, 128.7, 128.6, 128.0,
127.8, 126.4, 82.8, 65.4, 58.4, 51.2, 48.0 ppm; m=z (ESI): calcd. for C34H26Cl4O2
[M þ Na]þ 631.
=
Compound 2e
1
White oil; H NMR: dH 2.27 (dd, J ¼ 14.4, 5.4 Hz, 1H, H5), 2.74 (dd, J ¼ 14.4,
12 Hz, 1H, H5), 3.52–3.57 (m, 1H, H4), 3.65 (d, J ¼ 12.0 Hz, 1H, H2), 3.88 (dd,
J ¼ 9.6, 12.0 Hz, 1H, H3), 4.92 (s, 1H, OH), 6.29 (d, J ¼ 16.2 Hz, 1H, Hvinyl), 6.45
(d, J ¼ 15.6 Hz, 1H, Hvinyl), 6.81 (d, J ¼ 15.6 Hz, 1H, Hvinyl), 7.16–7.37 (m, 17H,
Ph-H, Hvinyl); 13C NMR: dC 201.8 (C O), 145.8, 142.8, 142.3, 138.3, 135.6, 134.9,
=
134.8, 134.6, 134.3, 130.9, 130.2, 129.9, 129.8, 128.2, 128.0, 127.9, 127.7, 127.5,
127.4, 126.9, 126.8, 126.4, 126.3, 126.2, 125.1, 82.8, 65.2, 58.3, 51.3, 48.2 ppm; m=z
(ESI): calcd. for C34H26Cl4O2 [M þ Na]þ 631.
Compound 2f
1
White solid, mp 136–138 ꢀC; H NMR: dH 2.21 (dd, J ¼ 14.4, 5.4 Hz, 1H, H5),
2.42 (dd, J ¼ 14.6, 11.3 Hz, 1H, H5), 2.75–2.82 (m, 1H, H4), 2.89 (d, J ¼ 12.1 Hz, 1H,
H2), 3.12 (dd, J ¼ 10.0, 12.1 Hz, 1H, H3), 5.19 (s, 1H, OH), 6.33 (d, J ¼ 16.2 Hz, 1H,
H
vinyl), 6.49 (d, J ¼ 16.2 Hz, 1H, Hvinyl), 6.72 (d, J ¼ 16.2 Hz, 1H, Hvinyl), 7.21–7.36
(m, 17H, Ph-H, Hvinyl); 13C NMR: dC 202.5 (C O), 141.3, 140.0, 138.7, 138.3,
136.3, 135.6, 135.3, 134.8, 133.7, 133.4, 132.2, 131.6, 130.2, 129.8, 129.4, 128.9,
128.6, 127.6, 127.0, 126.8, 125.4, 83.0, 48.0, 40.1, 29.7, 28.5 ppm; m=z (ESI): calcd.
for C34H26Cl4O2 [M þ Na]þ 631.
=
Compound 2g
1
White solid, mp 188–190 ꢀC; H NMR: dH 2.26 (dd, J ¼ 15.0, 5.4 Hz, 1H, H5),
2.73 (dd, J ¼ 14.6, 11.3 Hz, 1H, H5), 3.56–3.75 (m, 2H, H4, H2), 3.71 (dd, J ¼ 10.0,

826
J.-T. LI, C. DU, AND X.-L. ZHAI
12.1 Hz, 1H, H3), 5.05 (s, 1H, OH), 6.17 (d, J ¼ 16.1 Hz, 1H, Hvinyl), 6.42 (d,
J ¼ 15.8 Hz, 1H, Hvinyl), 6.83 (d, J ¼ 15.8 Hz, 1H, Hvinyl), 7.13–7.40 (m, 19H,
Ph-H, Hvinyl); 13C NMR: dC 202.7 (C O), 142.6, 142.4, 140.5, 136.8, 136.6, 134.4,
=
133.4, 132.5, 131.9, 129.6, 129.2, 129.1, 128.8, 128.6, 128.5, 127.8, 127.6, 127.2,
126.8, 126.5, 82.9, 65.4, 59.1, 51.6, 48.2 ppm; m=z (ESI): calcd. for C34H28Cl2O2
[M þ Na]þ 561.
Compound 2h
White solid, mp 196–198 ꢀC; 1H NMR: dH 2.24–2.31 (m, 7H, 2CH3, H5),
2.67–2.70 (m, 1H, H5), 3.55–3.66 (m, 2H, H4, H2), 3.83 (dd, J ¼ 7.2, 16.8 Hz, 1H,
H3), 5.11 (s, 1H, OH), 6.20 (d, J ¼ 16.2 Hz, 1H, Hvinyl), 6.36 (d, J ¼ 15.6 Hz, 1H, Hvi-
nyl), 6.77 (d, J ¼ 15.6 Hz, 1H, Hvinyl), 7.08–7.28 (m, 19H, Ph-H, Hvinyl); 13C NMR: dC
=
203.2 (C O), 144.1, 143.8, 140.7, 137.3, 136.6, 134.2, 133.9, 132.8, 131.3, 130.7,
129.6, 129.2, 128.8, 128.6, 128.4, 127.9, 127.7, 126.5, 125.8, 82.8, 65.1, 59.1, 51.5,
48.4, 21.5, 21.2 ppm; m=z (ESI): calcd. for C36H34O2 [M þ Na]þ 521.
Compound 2i
1
White solid, mp 163–165 ꢀC; H NMR: dH 2.23–2.30 (m, 1H, H5), 2.67–2.72
(m, 1H, H5), 3.52–3.86 (m, 9H, 2OCH3, H4, H2, H3), 5.18 (s, 1H, OH), 6.13 (d,
J ¼ 15.6 Hz, 1H, Hvinyl), 6.27 (d, J ¼ 15.6 Hz, 1H, Hvinyl), 6.41 (d, J ¼ 16.2 Hz, 1H,
vinyl), 6.78–7.34 (m, 19H, Ph-H, Hvinyl); 13C NMR: dC 203.1 (C O), 161.9,
=
H
159.1, 158.6, 143.8, 140.8, 136.9, 133.9, 132.6, 131.7, 130.7, 130.3, 129.6, 129.5,
128.8, 128.6, 128.3, 128.0, 127.9, 127.7, 126.6, 126.2, 114.3, 114.1, 113.9, 113.7,
82.8, 65.5, 59.2, 55.3, 51.6, 48.4 ppm; m=z (ESI): calcd. for C36H34O4 553 [M þ Na]þ.
ACKNOWLEDGMENT
The Natural Science Foundation of Hebei Province (B2006000969), China,
supported the project.
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