N. Brosse et al. / Tetrahedron Letters 43 (2002) 2009–2011
2011
References
7.37–7.17 m (5H); 5.83–5.71 m (1H); 5.24–5.10 m (3H);
3.81 d (J=4.4 Hz, 2H); 3.72 s (0.35H); 3.69 s (2.55H);
1.42 d (J=6.7 Hz, 0.35H); 1.31 d (J=6.7 Hz, 2.55H). 13C
NMR: l 170.4; 169.7; 165.3; 164.6; 156.3; 136.6; 135.9;
135.3; 129.5; 129.4; 128.5; 124.9; 124.6; 67.4; 56.5; 55.1;
53.5; 53.1; 43.1; 42.7; 14.6; 14.3.
1. This nomenclature was described by Spatola, A. F.
Chemistry and Biochemistry of Amino Acids, Peptides and
Proteins; Marcel Dekker: New York, Tokyo, 1984; pp.
17–37.
2. (a) Grupe, R.; Baeck, B.; Niedrich, H. J. Prackt. Chem.
1972, 314, 751–758; (b) Niedrich, H. Chem. Ber. 1965, 98,
3451–3461.
10. The (L,L)-diastereoisomer of 7e was synthesised starting
from (R)-methyl-2-hydroxypropionate.
11. Brosse, N.; Jamart-Gre´goire, B. Tetrahedron Lett. 2002,
43, 249–251.
3. (a) Dupond, V.; Lecoq, A.; Mangeot, J.-P.; Aubry, A.;
Boussard, G.; Marraud, M. J. Am. Chem. Soc. 1993, 115,
8898–8906; (b) Lecoq, A.; Dupond, V.; Marraud, M.;
Aubry, A. Peptides 1990, 383–384; Lecoq, A.; Marraud,
M.; Aubry, A. Tetrahedron Lett. 1991, 32, 2765–2768;
Garrouste, P.; Pawlowski, M.; Tonnaire, T.; Sicsic, S.;
Dumy, P.; de Rosny, E.; Reboud-Ravaux, M.; Fulcrand,
P.; Martinez, J. Eur. J. Med. Chem. 1998, 33, 423–436.
4. Himmer, H.; Nelson, V.; Robinson, W.; Go¨tz, M. Liebigs
Ann. Chem. 1973, 1789–1796.
5. Aubry, A.; Del Duca, V.; Pedone, C.; Zerkout, S.; Mar-
raud, M. Acta Crystallogr. 1999, C55, 439–441.
6. (a) Brosse, N.; Pinto, M.-F.; Jamart-Gre´goire, B. J. Org.
Chem. 2000, 65, 4370–4374; (b) Brosse, N.; Pinto, M.-F.;
Bodiguel, J.; Jamart-Gre´goire, B. J. Org. Chem. 2001, 66,
2869–2873.
12. NMR spectra15 of compound 8 R1=Me, R2=Me, R3=
Me: 1H NMR (400 MHz, CDCl3): l 7.40–7.21 m (5H);
5.56 d (J=8.2 Hz, 1H); 5.17–5.00 m (2H); 4.65–4.55 m
(1H); 4.48–4.55 m (1H); 3.70 s (1H); 1.54 s (9H); 1.47 s
(9H); 1.39 d (J=7.4 Hz, 3H); 1.27 pd (3H). 13C NMR: l
(ppm) 174.9; 170.6; 155.4; 150.8; 150.2; 136.8; 128.8;
128.4; 85.9; 85.7; 67.0; 58.1; 52.6; 47.4; 28.2; 27.9; 19.6;
14.4. NMR spectra15 of compound 9 R1=H, R2=Me,
R3=Me: 1H NMR (400 MHz, CDCl3): l (ppm) 7.43–
7.23 m (5H); 5.17 s (2H); 4.65 q (J=7.4 Hz, 1H); 4.39 s
(2H); 3.63 s (3H); 1.50 s (9H); 1.49 s (9H); 1.40 s (9H);
1.31 d (J=7.2, 3H). 13C NMR: l (ppm) 170.9; 169.9;
153.9; 151.7; 150.5; 135.9; 128.7; 128.4; 85.6, 85.5; 83.5;
68.9; 56.7; 52.4; 47.8; 28.1; 28.0; 14.4; 14.0.
13. NMR spectra15 of compound 10 R1=H, R2=Me, R3=
Me: 1H NMR (400 MHz, CDCl3): l 7.39–7.23 m (5H);
5.71–5.61 m (1H); 5.35–5.25 m (1H); 5.15–5.05 m (3H);
4.45–3.85 m (2H); 3.69 s (3H); 1.47 s (9H); 1.40 d (J=7.2
Hz, 3H). 13C NMR: l 173.0; 172.9; 156.7; 155.1; 136.8;
129.0, 128.8; 128.4; 128.4; 82.6; 67.2; 54.2; 52.7; 42.8;
28.3; 14.1.
14. Stafford, J. A.; Brackeen, M. F.; Karanewsky, D. S.;
Valvano, N. L. Tetrahedron Lett. 1993, 34, 7873–7876.
15. The observation of two sets of resonance for some groups
suggested that the compounds were present as two Z and
E isomers (see Ref. 6).
7. Pinto, M.-F.; Brosse, N.; Jamart-Gre´goire, B. Synth.
Commun. 2002, 32, in press.
8. General procedure: To a solution of 6 (3 mmol), PPh3
(4.5 mmol), 2 (4.5 mmol) in dry THF (50 mL) and under
nitrogen was added in one portion of DBAD (4.5 mmol)
with stirring at 0–5°C. The resulting solution was stirred
at room temperature for 2 h (monitored by TLC until
completion) and concentrated in vacuo. The residue was
evaporated and the residue was chromatographed on
silica gel using a mixture hexane/EtOAc as eluent.
9. NMR spectra15 of compound 7 R1=H, R2=Me, R3=
Me: 1H NMR (400 MHz, CDCl3): l 7.93–7.62 m (4H);