K. E. Harding, J. M. Southard / Tetrahedron: Asymmetry 16 (2005) 1845–1854
1853
26
of 23 as a white foam. ½aꢁ ¼ þ19.0 (c 0.59, CHCl3),
;
1759, 1715, 1695 cmꢀ1 1H NMR (200 MHz, CDCl3,
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D
lit.2m [a]D = +19.8 (c 0.56, CHCl3); IR (CHCl3) 3392,
3. (a) Vorbruggen, H.; Krolikkiewicz, K.; Bennua, B. Chem.
¨
J. Org. Chem. 1974, 39, 3654–3674.
¨
Ber. 1981, 114, 1234; (b) Vorbruggen, H.; Niedballa, U.
60 ꢁC) d 1.89 (d, J = 1 Hz, 3H, 5-CH3), 2.07, 2.08 (s,
2 · 3H, OCOCH3), 3.80 (s, 3H, CO2CH3), 4.37 (dd,
J = 5, 4 Hz, 1H, H-40), 4.81 (dd, J = 9, 4 Hz, 1H, H-
50), 5.14 (s, 2H, CH2Ph), 5.27 (t, J = 6 Hz, 1H, H-20),
5.52 (t, J = 6 Hz, 1H, H-30), 5.80 (m, 1H, NH), 5.93
(d, J = 6 Hz, 1H, H-10), 7.05 (d, J = 0.6 Hz, 1H, H-6),
4. Nishimura, T.; Iwai, I. Chem. Pharm. Bull. 1964, 12, 352–
356.
5. Nasman, J.-A.; Pensar, K. G. Synthesis 1985, 786–787.
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1180; (i) Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P.
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F.; Rassu, G.; Spanu, P.; Pinna, L. Tetrahedron Lett. 1995,
36, 1941–1944; (k) Casiraghi, G.; Rassu, G. Synthesis 1994,
607–626; (l) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.
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Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. Tetrahedron
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Colombo, L.; Rassu, G.; Spanu, P. J. Org. Chem. 1991, 56,
6523–6527; (q) Casiraghi, G.; Colombo, L.; Rassu, G.;
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G.; Colombo, L.; Rassu, G.; Spanu, P. J. Org. Chem. 1990,
55, 2565–2567; (s) Casiraghi, G.; Rassu, G.; Pinna, L.;
Spanu, P.; Culeddu, N.; Fava, G. G.; Ferrari, M. B.; Pelosi,
G. Tetrahedron 1992, 48, 727–742; (t) Casiraghi, G.;
Colombo, L.; Rassu, G.; Spanu, P.; Fava, G. G.; Belicchi,
M. F. Tetrahedron 1990, 46, 5807–5824; (u) Rassu, G.;
Spanu, P.; Casiraghi, G.; Pinna, L. Tetrahedron 1991, 47,
8025–8030; (v) Rassu, G.; Casiraghi, G.; Spanu, P.; Pinna,
L. Tetrahedron: Asymmetry 1992, 3, 1035–1048; (w) Casi-
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603–604.
1
7.33 (br s, 5H, C6H5), 7.85 (br s, 1H, N3H); H NMR
(400 MHz, CDCl3) d 1.90 (s, 3H, 5-CH3), 2.09, 2.10 (s,
2 · 3H, OCOCH3), 3.81 (s, 3H, CO2CH3), 4.39 (approx.
t, J = 4.3 Hz, 1H, H-40), 4.83 (dd, J = 8.3, 3.5 Hz, 1H,
H-50), 5.12 (d, J = 12.2 Hz, 1H, CH(Ha)Ph), 5.16 (d,
J = 12.2 Hz, 1H, CH(Hb)Ph), 5.27 (t, J = 6.0 Hz, 1H,
H-20), 5.52 (t, J = 5.7 Hz, 1H, H-30), 5.80 (br d, 1H,
NH), 5.93 (d, J = 5.8 Hz, 1H, H-10), 7.05 (br s, 1H,
H-6), 7.36 (br s, 5H, C6H5), 8.36 (br d, 1H, N3H);
13C NMR (50 MHz, CDCl3) d 10.8 (5-CH3), 18.7
(2OCOCH3), 51.2 (CO2CH3), 54.5 (C-50), 65.5 (CH2Ph),
69.1 (C-30 or C-40), 71.4 (C-40 or C-30), 80.2 (C-20), 87.7
(C-10), 110.0 (C-5), 127.0, 127.1, 127.6 (Ph), 135.7 (C-6),
136.2 (Ph), 49.8 (C-2), 155.4 (NCO2), 162.5 (C-4), 168.3,
168.4 (2OCOCH3), 168.6 (CO2CH3); FABHRMS
(NBA) m/e, found: 534.1727; calcd for C24H27N3O11:
534.1723 (M+).
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