1
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cyclopentyl)pyrimidin-2(1H)-one (29b)
1
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TFA solution in water (4 mL). After 24 h of stirring at room tem-
perature and evaporation of the solvent, the resulting yellow pre-
cipitate was washed with EtOAc (5 mL) and then with diethyl ether.
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1
Compound (ꢀ)-29b was obtained as a white solid (54 mg, 62%). H
12. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int.
6
NMR (250 MHz, CD
3
OD)
d
7.88 (d, 1H, J¼7.5 Hz, H ), 6.04 (d, 1H,
Ed. 2002, 41, 2596–2599; (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org.
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7558–7564.
0
0
2
5
1
J¼7.5 Hz, H ), 4.65 (q, 1H, J¼9.4 Hz, H ), 4.42 (q, 1H, J¼9.4 Hz, H ),
0
0
0
0
6
5
7
3
3
.47 (s, 4H, H þH ), 2.06–1.97 (m, 2H, H þH ), 1.71–1.48 (m, 2H,
0 0
3 6 13 4 2
H þH ). C NMR (62.9 MHz, CD
3
OD)
d
161.1 (C, C ), 149.6 (C, C ),
14. Candelon, N.; Laste
cou e` res, D.; Khadri Diallo, A.; Aranzaes, J. R.; Astruc, D.;
´
0
0
6
5
2
5
1
48.2 (CH, C ), 94.9 (CH, C ), 74.1 (CH, C ), 68.0 (CH
2
, C ), 67.8 (CH
, C ), 33.3 (CH
(M þH) 256.1297, found 256.1285.
2
,
Vincent, J. M. Chem. Commun. 2008, 741–743.
0
0
0
0
0
7
1
4
3
6
1
5. Depr e´ s, J. P.; Greene, A. E. J. Org. Chem. 1984, 49, 928–931.
C ), 65.8 (CH, C ), 45.0 (C, C ), 37.7 (CH
2
2
, C ). HRMS
þ
16. Kang, J. H.; Chung, H. E.; Kim, S. Y.; Kim, Y.; Lee, J.; Lewin, N. E.; Pearce, L. V.;
Blumberg, P. M.; Marquez, V. E. Bioorg. Med. Chem. 2003, 11, 2529–2539.
(
ESI): m/z calcd for C11
cknowledgements
H
18
N
3
O
4
1
7. Trost, B. M.; Ball, Z. T.; J o¨ ge, T. A. J. Am. Chem. Soc. 2002, 124, 7922–7923.
18. (a) Ewing, D. F.; Goethals, G.; Mackenzie, G.; Martin, P.; Ronco, G.; Vanbae-
ꢀ
linghem, L.; Villa, P. J. Carbohydr. Chem. 1999, 441–450; (b) Ewing, D. F.; Goe-
thals, G.; Mackenzie, G.; Martin, P.; Ronco, G.; Vanbaelinghem, L.; Villa, P.
Carbohydr. Res. 1999, 190–196.
These studies were supported by a grant from Aventis Pharma
Sanofi-Aventis group) and Bayer Pharma as part of a multi-or-
19. Joubert, N.; Schinazi, R. F.; Agrofoglio, L. A. Tetrahedron 2005, 61, 11744–11750.
(
2
0. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004–2021.
21. (a) Deiters, A.; Cropp, T. A.; Mukerji, M.; Chin, J. W.; Anderson, J. C.; Schultz, P. G.
J. Am. Chem. Soc. 2003, 125, 11782–11783; (b) Lee, L. V.; Mitchell, M. L.; Huang,
S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588–
ganism call for proposals. The ICIQ Foundation is gratefully ac-
knowledged for financial support. S.D.-G. thanks the support of the
Ministerio de Educaci o´ n y Ciencia (Spain) through the program
Torres Quevedo for young researchers. SPN is an ICREA Research
Professor. Authors acknowledge Dr. D. Deville-Bonne (Institut J.
Monod, Paris, France) Pr D. Garin (CRSSA, La Tronche, France), Pr R.
Snoeck (Rega Institute, Leuven, Belgium) for biological evaluations.
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