Total synthesis of ( )-divanillyltetrahydrofuran ferulate
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11b, which were hydrogenated with 10% palladium
on charcoal catalyst to obtain the key intermediate
meso-shonanin 12a and threo-( )-shonanin 12b,
respectively (scheme 2).17–19
Ferulaic acid was esterified with MeOH, followed
by protection with MOMCl to produce the com-
pound 13. Hydrolysis of the ester 13 gave the inter-
mediate 14 (scheme 3).
As shown in scheme 4, the condensation of the
intermediate meso-12a with the acid 14 employing
DCC and DMAP, followed by deprotection of MOM
group using HCl at room temperatrue furnished the
target product erythro-( )-2. Following the proce-
dure described for the preparation of erythro-( )-2,
and starting with threo-( )-12b, compound threo-
( )-1 was obtained. The spectral data of threo-( )-1
were in agreement with those found in the litera-
ture.1,20
17. Wang Q, Yang Y, Li Y, Yu W and Hou Zi J 2006
Tetrahedron 62 6107
18. Fang J M, Hsu K C and Cheng Y S 1989 Phytochemi-
stry 28 3553
19. meso-Shonanin 12a: IR (KBr/cm–1): 3339, 2916,
1609, 1520, 1253, 1038, 928. 1H NMR (CDCl3,
500 MHz) δ: 2⋅44−2⋅50 (m, 4H, 2 × ArCH2CH),
2⋅78–2⋅85 (m, 2H, 2 × ArCH2CH), 3⋅61 (dd, 2H,
J = 8⋅0, 4⋅5 Hz, CH2O), 3⋅75 (dd, 2H, J = 8⋅0, 6⋅0 Hz,
CH2O), 3⋅82 (s, 6H, 2 × OCH3), 6⋅50–6⋅82 (m, 6H,
ArH). 13C NMR (CDCl3, 125 MHz) δ: 33⋅2 (C-7′, C-
7″), 43⋅8 (C-3, C-4), 55⋅9 (2 × OCH3), 72⋅3 (C-2, C-
5), 111⋅2 (C-2′, C-2″), 114⋅4 (C-5′, C-5″), 121⋅3 (C-
6′, C-6″), 132⋅5 (C-1′, C-1″), 143⋅9 (C-4′, C-4″),
146⋅5 (C-3′, C-3″). HRMS calcd for C20H28NO5
(M + NH+4): 362⋅1962; found: 362⋅1959. threo-( )-
Shonanin 12b: IR (KBr/cm–1): 3403, 2918, 1604,
Acknowledgements
This work was financially supported by Taishan
Scholar Project of Shandong Province (No.
2005011036), China and Specialized Research Fund
for the Doctoral Program of Higher Education of
China (No. 20093719120004) and Open Foundation
of Chemical Engineering Subject, Qingdao Univer-
sity of Science and Technology, China.
1
1515, 1261, 1042. H NMR (CDCl3, 500 MHz) δ:
2⋅11–2⋅18 (m, 2H, 2 × ArCH2CH), 2⋅51−2⋅61 (m, 4H,
2 × ArCH2CH), 3⋅53 (dd, 2H, J = 9⋅0, 5⋅5 Hz, CH2O),
3⋅82 (s, 6H, 2 × OCH3), 3⋅92 (dd, 2H, J = 9⋅0, 6⋅5 Hz,
CH2O), 6⋅51–6⋅90 (m, 6H, ArH). 13C NMR (CDCl3,
125 MHz) δ: 39⋅2 (C-7′, C-7″), 46⋅5 (C-3, C-4), 55⋅8
(2 × OCH3), 73⋅3 (C-2, C-5), 111⋅1 (C-2′, C-2″),
114⋅1 (C-5′, C-5″), 121⋅3 (C-6′, C-6″), 132⋅3 (C-1′,
C-1″), 143⋅9 (C-4′, C-4″), 146⋅4 (C-3′, C-3″). HRMS
calcd for C20H28NO5 (M + NH+4): 362⋅1962; found:
362⋅1964.
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20. erythro-( )-Divanillyltetrahydrofuran ferulate 2: IR
(KBr/cm–1): 3410, 2935, 1710, 1612, 1523, 1245,
1
1236, 928. H NMR (DMSO-d6, 500 MHz) δ: 2⋅45–