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PAPER
1H NMR (500 MHz, CD3OD): d = 7.42 (d, J = 8.9 Hz, 2 Harom, o-
CH), 6.93 (d, J = 8.9 Hz, 2 Harom, m-CH), 3.78 (s, 3 H, ArOCH3),
2.98 and 2,63 (m, 2 H, H-3), 2.59 and 2.55 (m, 2 H, H-4).
13C NMR (125 MHz, CD3OD): d = 177.8 (C-5), 173.8 (C-1), 161.4
(MeOCarom), 131.6 (Carom), 127.8 (o-CHarom), 114.9 (m-CHarom),
88.4 (C-2), 55.8 (ArOCH3), 33.9 (C-3), 29.1 (C-4).
MS (EI, 70 eV): m/z (%) = 236 (7, [M+]), 208 (3), 191 (94), 163 (4),
135 (93), 121 (4), 98 (13), 83 (42), 77 (24).
HRMS-EI: m/z calcd for [M – CO2H]+ C11H11O3: 191.0707; found:
H-6), 1.65 and 0.83 (m, 2 H, H-4), 1.62 and 0.98 (m, 2 H, H-3), 1.45
(m, 1 H, H-8), 1.45 (m, 1 H, H-5), 1.38 (m, 1 H, H-2), 0.88 (d,
J = 6.5 Hz, 3 H, H-7), 0.74 (d, J = 7.0 Hz, 3 H, H-10), 0.54 (d,
J = 7.0 Hz, 3 H, H-9).
13C NMR (125 MHz, CDCl3): d (acid part) = 175.1 (C-5), 169.7 (C-
1), 138.2 (Carom), 128.6 (CHarom, para to Carom), 128.5 (m-CHarom),
124.9 (o-CHarom), 33.1 (C-4), 28.2 (C-3); d (menthyl part) = 76.8
(C-1), 46.8 (C-2), 40.3 (C-6), 34.0 (C-4), 31.3 (C-5), 25.9 (C-8),
23.2 (C-3), 21.9 (C-7), 20.5 (C-10), 15.9 (C-9).
191.0699.
Acknowledgment
4-(4-Methoxyphenyl)-4-oxobutyric Acid (3d)
Compound 3d was in 32% yield as a colorless powder; mp 140–
143 °C.
The authors thank the Estonian Ministry of Education and Research
for grant 0142725s06, Estonian Science Foundation for financial
support (Grant No: 5628 and 6778) and Competence Centre for
Cancer Research for support.
IR (KBr): 2842, 1698, 1667, 1602, 1574, 1514, 1426, 1270, 1247,
1174, 1028, 943, 834 cm–1.
1H NMR (500 MHz, CD3OD): d = 7.96 (d, J = 8.8 Hz, 2 Harom, o-
CH), 6.98 (d, J = 8.8 Hz, 2 Harom, m-CH), 3.85 (s, 3 H, OCH3), 3.24
(t, J = 6.4 Hz, 2 H, H-3), 2.67 (t, J = 6.4 Hz, 2 H, H-2).
13C NMR (125 MHz, CD3OD): d = 199.1 (C-4), 176.7 (C-1), 165.3
(MeOCarom), 131.4 (o-CHarom), 130.9 (Carom), 114.8 (m-CHarom),
56.0, (ArOCH3), 34.0 (C-3), 29.0 (C-2).
References
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R.; Duguay, D.; Touraille, F.; Caron, D. Tetrahedron:
Asymmetry 2004, 15, 863. (d) Pitacco, G.; Sessanta o Santi,
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Ishibashi, H. J. Org. Chem. 2005, 70, 4569. (e) Masaki, H.;
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(b) Lee, K.-H.; Huang, B.-R.; Tseng, C.-C. Bioorg. Med.
Chem. Lett. 1999, 9, 241.
(5) Paju, A.; Laos, M.; Jõgi, A.; Päri, M.; Jäälaid, R.; Pehk, T.;
Kanger, T.; Lopp, M. Tetrahedron Lett. 2006, 47, 4491.
(6) Stetter, H.; Schlenker, W. Tetrahedron Lett. 1980, 21, 3479.
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(8) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
(9) Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis, Vol.
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(10) (a) Paju, A.; Kanger, T.; Pehk, T.; Müürisepp, A.-M.; Lopp,
M. Tetrahedron: Asymmetry 2002, 13, 2439. (b) Paju, A.;
Kanger, T.; Pehk, T.; Lindmaa, R.; Müürisepp, A.-M.; Lopp,
M. Tetrahedron: Asymmetry 2003, 14, 1565. (c) Paju, A.;
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MS (EI, 70 eV): m/z (%) = 208 (9, [M+]), 135 (100), 123 (7), 107
(8), 92 (10), 77 (15).
g-Phenyl-g-lactone Acid Menthol Esters 9a and 9b
Diastereomeric esters were synthesized separately from R- and S-
enantiomers of g-lactone acids 1a with (1R,2S,5R)-(–)-menthol ac-
cording to the known procedure.10b Enantiomeric purity of diaste-
reomers was determined from 1H NMR spectra in the 0.5–0.6 ppm
area.
(R)-5-Oxo-2-phenyltetrahydrofuran-2-carboxylic Acid
(1R,2S,2R)-2-Isopropyl-5-methylcyclohexyl Ester (9a)
Lactone acid menthyl ester 9a was obtained according to the known
procedure.10b
1H NMR (500 MHz, CDCl3): d (acid part) = 7.50 (m, 2 Harom, o-
CH), 7.39 (m, 2 Harom, m-CH), 7.36 (m, 1 Harom, p-CH), 3.05 and
2.57 (m, 2 H, H-4), 2.61 (m, 2 H, H-3); d (menthyl part) = 4.68 (dt,
J = 4.5, 2 × 10.9 Hz, H-1), 1.86 and 0.92 (m, 2 H, H-6), 1.66 and
0.82 (m, 2 H, H-4), 1.63 and 0.99 (m, 2 H, H-3), 1.47 (m, 1 H, H-
8), 1.45 (m, 1 H, H-5), 1.36 (m, 1 H, H-2), 0.86 (d, J = 6.5 Hz, 3 H,
H-7), 0.76 (d, J = 7.0 Hz, 3 H, H-10), 0.60 (d, J = 7.0 Hz, 3 H, H-9).
13C NMR (125 MHz, CDCl3): d (acid part) = 175.0 (C-5), 169.9 (C-
1), 137.9 (Carom), 128.7 (CHarom, para to Carom), 128.5 (m-CHarom),
125.2 (o-CHarom), 33.0 (C-4), 28.2 (C-3); d (menthyl part) = 76.8
(C-1), 46.8 (C-2), 40.2 (C-6), 34.0 (C-4), 31.3 (C-5), 25.9 (C-8),
23.1 (C-3), 21.9 (C-7), 20.6 (C-10), 15.9 (C-9).
(S)-5-Oxo-2-phenyltetrahydrofuran-2-carboxylic Acid
(1R,2S,2R)-2-Isopropyl-5-methylcyclohexyl Ester (9b)
Lactone acid menthyl ester 9b was obtained according to the known
procedure.10b
1H NMR (500 MHz, CDCl3): d (acid part) = 7.49 (m, 2 Harom, o-
CH), 7.39 (m, 2 Harom, m-CH), 7.36 (m, 1 Harom, p-CH), 3.10 and
2.55 (m, 2 H, H-4), 2.65 and 2.55 (m, 2 H, H-3); d (menthyl
part) = 4.67 (dt, J = 4.5, 2 × 10.9 Hz, H-1), 1.90 and 0.97 (m, 2 H,
Synthesis 2006, No. 18, 3031–3036 © Thieme Stuttgart · New York