Griesbeck and Bondock
559
Methyl (2S*,3S*) 2-(N-acetylamino)-3-hydroxy-3-phenyl-
propionate (erythro-4a)
8. S.L. Schreiber and A.H. Hoveyda. J. Am. Chem. Soc. 106,
7
200 (1984).
9
. H.A.J. Carless and A.F.E. Halfhide. J. Chem. Soc., Perkin
Trans. 1, 1081 (1992).
According to the above general procedure, bicyclic oxetane
a (0.44 g, 2 mmol) was cleaved hydrolytically in 3 h. Pre-
3
1
1
0. S.L. Schreiber, D. Desmaele, and J.A. Porco, Jr. Tetrahedron
Lett. 29, 6689 (1988).
1. S.L. Schreiber and J.A. Porco, Jr. J. Org. Chem. 54, 4721
(1989).
parative chromatography yielded 0.33 g (70%) of the product
–1
as a colorless oil. R = 0.34 (EA:H = 1:4). IR (film) (cm ):
f
3
500 (OH), 3370 (NH), 2983, 2894 (C-H), 1725 (COO), 1675
1
(CON), 1605 (Ph), 1445 (CH), 1018 (C-O). H NMR
1
1
2. R. Hambalek and G. Just. Tetrahedron Lett. 31, 4693 (1990).
3. C. Rivas and R.A. Bolivar. J. Heterocycl. Chem. 13, 1037
(
300 MHz, CDCl ) δ: 2.07 (s, 3H, CH CO), 3.97 (s, 3H,
3
3
OCH ), 4.45 (d, J = 9.7 Hz, 1H, CHN), 5.85 (d, J = 9.7 Hz,
3
(
1976).
1
H, CHOH), 6.37 (bs, 1H, NH), 7.28–7.35 (m, 5H, Harom).
1
1
4. G. Jones, II, H.M. Gilow, and J. Low. J. Org. Chem. 44, 2949
(1979).
5. T. Matsuura, A. Banba, and K. Ogura. Tetrahedron, 27, 1211
1
3
C NMR (75.5 MHz, CDCl ) δ: 23.7 (q), 52.4 (q), 75.4 (d,
3
C-2), 81.6 (d, C-3), 126.2 (s, C-5), 128.9 (d), 129.6 (d),
34.3 (s), 169.3 (s, CON), 170.3 (s, COO). Anal. calcd.
C H NO ): C 60.75, H 6.37, N 5.90; found: C 60.65, H
1
(
1971).
(
6
1
2
15
4
16. T. Nakano, C. Rivas, C. Perez, and J.M. Larrauri. J.
.42, N 5.85.
Heterocycl. Chem. 13, 173 (1976).
1
7. C. Rivas, D. Pacheco, F. Vargas, and J. Ascanio. J. Heterocycl.
Methyl (2S*,3S*) 2-(N-acetylamino)-3-hydroxy-3-phenyl-
propionate (erythro-7a)
According to the above general procedure, bicyclic
oxetane 6a (0.47 g, 2 mmol) was cleaved hydrolytically in
Chem. 18, 1065 (1981).
18. T. Nakano, W. Rodriquez, S.Z. de Roche, J. Larrauri, C. Rivas,
and P. Pérez. J. Heterocycl. Chem. 17, 1777 (1980).
19. Y. Ito, M. Ji-Ben, S. Suzuki, Y. Kusunaga, T. Matsuura, and K.
Fukuyama. Tetrahedron Lett. 26, 93 (1985).
4
h. Preparative chromatography yielded 0.32 g (65%) of the
2
0. A.G. Griesbeck, M. Fiege, and J. Lex. Chem. Commun. 589
2000).
product as a colorless oil. R = 0.33 (EA:H = 1:4). MS (EI,
f
+
+
(
7
0 eV) m/z (%): 249 (M – H , 4), 236 (M – Me, 8), 202
2
+
21. As components in vancomycin and related cyclopeptides:
A.V.R. Rao, M.K. Gurjar, K.L. Reddy, and A.S. Rao. Chem.
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22. T. Kimura, V.P. Vassilev, G.-J. Shen, and C.-H. Wong. J. Am.
Chem. Soc. 119, 11 734 (1997).
2
2
2
2
2
(
8), 192 (M – CO Me, 15), 191 (78), 160 (10), 131 (100),
2
–
1
1
05 (50), 91 (20), 77 (30), 51 (10). IR (film) (cm ): 3500
(
1
OH), 3320 (NH), 2988 (C-H), 1720 (COO), 1680 (CON),
580 (Ph), 1440 (CH), 1025 (C-O). H NMR (300 MHz,
1
CDCl ) δ: 1.23 (s, 3H, CH ), 2.12 (s, 3H, CH CO), 3.79 (s,
3
3
3
3. M.A. Blaskovich, G. Evindar, N.G.W. Rose, S. Wilkinson, Y.
Luo, and G.A. Lajoie. J. Org. Chem. 63, 3631 (1988).
4. F.A. Davis, V. Srirajan, D.L. Fanelli, and P. Portonovo. J. Org.
Chem. 65, 7663 (2000).
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(1999).
6. D.A. Evans, J.M. Janey, N. Magomedov, and J.S. Tedrow.
Angew. Chem. Int. Ed. 40, 1884 (2001).
7. R.S. Singh and R.M. Singh. Indian J. Chem. Sect. B: Org.
Chem. Incl. Med. Chem. 39, 688 (2000).
3
H, OCH ), 4.06 (s, 1H, CHOH), 7.28–7.35 (m, 5H, Harom).
3
1
3
C NMR (75.5 MHz, CDCl ) δ: 13.5 (q), 21.4 (q), 21.4 (q),
3
2
5
3.4 (q), 47.7 (s, C-2), 49.1 (d, C-3), 52.9 (q), 127.6 (s, C-
), 128.4 (d), 129.6 (d), 133.5 (s), 169.9 (s, CON), 179.4 (s,
COO). HR-MS calcd. (C H NO ): 251.1254; found:
1
3
17
4
2
51.1249.
Ac knowle dge m e nts
2
2
8. A.G. Griesbeck and H. Heckroth. Synlett, 131 (2002).
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Padyukova, K.F. Turchin, and V.L. Florentiev. Tetrahedron, 25,
This work has been financially supported by the Deutsche
Forschungsgemeinschaft, the Fonds der Chemischen
Industrie. Amino acids were obtained as gifts from Degussa
AG. Samir Bondock expresses his thanks to the Egyptian
government for a Ph.D. grant (1999–2003).
3
3
3
Re fe re nc e s
3
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3
4
5
6
7
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(
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©
2003 NRC Canada