1
236
A. Kar, N. P. Argade
SHORT PAPER
1
H NMR (CDCl , 200 MHz): d = 1.15–2.10 (m, 10 H), 2.50–2.70
(6) Hill, R. H.; Foley, P. J.; Gardella, L. A. J. Org. Chem. 1967,
32, 2330.
3
(
m, 1 H), 2.70–2.90 (m, 1 H), 3.35–4.00 (m, 8 H), 4.60 (br s, 1 H),
6
.31 (br s, 1 H).
(7) (a) Boeckman, R. K. Jr.; Naegely, P. C.; Arthur, S. D. J. Org.
Chem. 1980, 45, 752. (b) Marx, J. N.; Minaskanian, G. J.
Org. Chem. 1982, 47, 3306. (c) Wexler, B. A.; Toder, B. H.;
Minaskanian, G.; Smith, A. B. III J. Org. Chem. 1982, 47,
1
3
C NMR (CDCl , 75 MHz): d = 19.2, 25.3, 30.4, 35.6, 35.8, 46.0,
8.7, 61.9, [64.3, 64.8 (1 C)], 66.2, [70.2, 70.4 (1 C)], 98.7, 116.6,
3
4
[
177.1, 178.4 (1 C)].
3
333. (d) Kobayashi, Y.; Tsuji, J. Tetrahedron Lett. 1981,
22, 4295. (e) Barreiro, E. J. Tetrahedron Lett. 1982, 23,
605. (f) Govindan, S. V.; Hudlicky, T.; Koszyk, F. J. J.
Anal. Calcd for C H O : C, 58.73; H, 7.74. Found: C, 58.77; H,
7
14
22
6
.69.
3
Org. Chem. 1983, 48, 3581. (g) Hewson, A. T.;
MacPherson, D. T. Tetrahedron Lett. 1983, 24, 647.
2
-Methylene-3-oxo-cyclopentanecarboxylic Acid [(±)-Sarkomy-
cin, 10]
(
1
h) Misumi, A.; Furuta, K.; Yamamoto, H. Tetrahedron Lett.
984, 25, 671. (i) Kodpinid, M.; Siwapinyoyos, T.;
A solution of 9 (572 mg, 2 mmol) in HCl (0.5 N; 15 mL) was stirred
at r.t. for 10 h and then extracted with CHCl (3 × 20 mL). The com-
bined organic layer was extracted with cold NaHCO (5%; 30 mL)
and the aqueous layer was reacidified with dil. HCl and again ex-
tracted with CHCl (2 × 10 mL). Concentration of the organic layer
gave essentially pure 10 as a thick oil; yield: 84 mg (30%).
3
Thebtaranonth, Y. J. Am. Chem. Soc. 1984, 106, 4862.
(j) Mikolajczyk, M.; Zurawinski, R.; Kielbasinski, P.
Tetrahedron Lett. 1989, 30, 1143; and references cited
therein 7a–j.
3
3
(
8) (a) Kozikowski, A. P.; Stein, P. D. J. Am. Chem. Soc. 1982,
104, 4023. (b) Froissant, J.; Huet, F.; Conia, J. M. Nouv. J.
Chim. 1983, 7, 699. (c) Vidal, J.; Huet, F. Tetrahedron Lett.
–
1
IR (CHCl ): 2943, 1723 cm .
3
1
H NMR (CDCl , 200 MHz): d = 2.10–3.20 (m, 4 H), 3.45–3.85 (m,
3
1
986, 27, 3733. (d) Froissant, J.; Vidal, J.; Guibe-Jampel,
1
H), 5.70 (d, J = 2 Hz, 1 H), 6.23 (d, J = 2 Hz, 1 H).
E.; Huet, F. Tetrahedron 1987, 43, 317. (e) Amri, H.;
Anal. Calcd for C H O : C, 60.00; H, 5.75. Found: C, 60.03; H,
5
Rambaud, M.; Villieras, J. Tetrahedron Lett. 1989, 30, 7381.
7
8
3
.70.
(9) (a) Samarat, A.; Fargeas, V.; Villieras, J.; Lebreton, J.; Amri,
H. Tetrahedron Lett. 2001, 42, 1273. (b) Samarat, A.;
Landais, Y.; Amri, H. Tetrahedron Lett. 2004, 45, 2049.
10) (a) Gogoi, S.; Argade, N. P. Tetrahedron 2004, 60, 9093.
Acknowledgment
(
(
5
6
(
(
b) Mondal, M.; Argade, N. P. Tetrahedron Lett. 2004, 45,
693. (c) Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2004,
9, 4563. (d) Mondal, M.; Argade, N. P. Synlett 2004, 1243.
e) Mangaleswaran, S.; Argade, N. P. Synthesis 2004, 1560.
f) Mhaske, S. B.; Argade, N. P. Tetrahedron 2004, 60,
A. K. thanks CSIR, New Delhi, for the award of a research fel-
lowship. N. P. A. thanks Department of Science and Technology,
New Delhi, for financial support.
3
417. (g) Kar, A.; Argade, N. P. Tetrahedron 2003, 59,
References
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(
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