SYNTHESIS
September 1998
1323
Table 3. Analytical and Spectroscopic Data of Compounds 2 and 3
Compound
[α]D20
1H NMR (300 MHz, CDCl3)
13C NMR (75 MHz, CDCl3)
(c, Solvent)
δ, J (Hz)
δ
2a
–43.0
3.99 (dd, J = 18.3, 5.5, 1H, CH2N), 4.09 (dd, J = 18.3, 43.00 (t, CH2N), 67.14 (t, PhCH2), 77.45 (d,
(2.0, CHCl3) 5.7, 1H, CH2N), 5.12 (s. 2H, PhCH2), 5.28 (d, J = 10.3, CHOCO), 116.61 (t, CH=CH2), 127.18, 128.11,
2H, CH=CHHt, NH), 5.31 (d, J = 17.1, 1H, CH=CH- 128.20, 128.47,128.55, 128.66 (6d, ArC), 135.62 (d,
Hc), 6.01 (ddd, J = 17.1, 10.6, 6.0, 1H, CH=CH2), 6.21 CH=CH2), 136.26, 138.20 (2s, quart. ArC), 156.23
(m, 1H, CHOCO), 7.35 (sbr, 10H, ArH)
(s, OCON), 169.05 (s, COO)
ent-2a
+ 42.1
3.99 (dd, J = 18.3, 5.5, 1H, CH2N), 4.08 (dd, J = 18.3, 42.99 (t, CH2N), 67.13 (t, PhCH2), 77.45 (d,
(0.5, CHCl3) 5.7, 1H, CH2N), 5.12 (s, 2H, PhCH2), 5.28 (d, J = 10.3, CHOCO), 116.61 (t, CH=CH2), 127.17, 128.10,
2H, CH=CHHt, NH), 5.31 (d, J = 17.3, 1H, CH=CH- 128.20, 128.47, 128.55, 128.65 (6d, ArC), 135.62 (d,
Hc), 6.01 (ddd, J = 17.3, 10.4, 5.9, 1H, CH=CH2), 6.23 CH=CH2), 136.26, 138.20 (2s, quart. ArC), 156.23
(m, 1H, CHOCO), 7.35 (sbr, 10H, ArH)
(s, OCON), 169.04 (s, COO)
2b
–4.3
1.45 [s, 9H, C(CH3)3], 3.52–3.62 (m, 4H, CH2OBn, 28.28 (q, CH3), 42.52 (t, CH2N), 71.07 (t, CH2O),
(1.0, CHCl3) CH2N), 4.53 (d, J = 12.2, 1H, PhCH2), 4.57 (d, J = 73.99 (t, PhCH2), 74.28 (d, CHOCO), 79.93 [s,
12.2, 1H, PhCH2), 5.01 (sbr, 1H, NH), 5.26 (d, J = C(CH3)3], 118.56 (t, CH=CH2), 127.62, 127.74,
11.0, 1H, CH=CHHt), 5.33 (d, J = 17.3, 1H, 128.41 (3d, ArC), 132.68 (d, CH=CH2), 137.75 (s,
CH=CHHc), 5.53 (dd, J = 11.0, 5.9, 1H, CHOCO), quart. ArC), 155.56 (s, OCON), 169.58 (s, COO)
5.82 (ddd, J = 17.1, 10.7, 6.1, 1H, CH=CH2), 7.26–
7.,37 (m, 5H, ArH)
2c
–1.24
1.35 (s, 3H, CH3), 1.41 (s, 3H, CH3), 3.80 (dd, J = 26.18 (q, CH3), 26.32 (q, CH3), 42.91 (t, CH2N),
(5.5, CHCl3) 8.4, 6.3, 1H, CH2O), 3.99–4.04 (m, 3H, CH2O, 65.58 (t, CH2O), 67.17 (t, PhCH2), 75.22 (d, CHOC),
CH2N), 4.21 (dt, J = 11.2, 6.2, 1H, CHOC), 5.12 (s, 76.34 (d, CHOCO), 110.05 [s, C(CH3)2], 119.71 (t,
2H, PhCH2), 5.29–5.40 (m, 4H, NH, CHOCO, CH=CH2), 128.11, 128.22, 128.55 (3d, ArC), 131.72
CH=CH2), 5.81 (ddd, J = 17.2, 10.6, 6.6, 1H, (d, CH=CH2), 136.22 (s, quart. ArC), 156.22 (s,
CH=CH2), 7.31–7.35 (m, 5H, ArH)
OCON), 169.02 (s, COO)
2d
–13.8
1.38 (s, 3H, CH3), 1.40 (s, 3H, CH3), 1.43 [s, 9H, 26.62 (q, CH3), 26.85 (q, CH3), 28.07 [s, C(CH3)3],
(3.6, CHCl3) C(CH3)3], 3.57 (dd, J = 10.3, 5.2, 1H, CH2OBn), 42.28 (t, CH2N), 70.26 (t, CH2O), 73.31 (t, PhCH2),
3.61 (dd, J = 10.3, 3.7, 1H, CH2OBn), 3.86 (d, J = 74.90 (d, CHOC), 78.48 (d, CHOC), 78.76 (d,
5.4, 2H, CH2N), 3.97 (dd, J = 8.1, 4.0, 1H, CHOC), CHOCO), 79.79 [s, C(CH3)3], 109.85 [s, C(CH3)2],
4.06 (ddd, J = 8.1, 5.2, 2.9, 1H, CHOC), 4.55 (d, J = 119.66 (t, CH=CH2), 127.53, 128.18 (2d, ArC),
12.4, 1H, PhCH2), 4.59 (d, J = 12.4, 1H, PhCH2), 131.38 (d, CH=CH2), 137.64 (s, quart. ArC), 155.31
4.91 (sbr, 1H, NH), 5.28 (d, J = 10.5, 1H, CH=CHHt), (s, OCON), 169.07 (s, COO)
5.32 (ddd, J = 17.4, 1.1, 1.1 Hz, 1H, CH=CHHc),
5.42 (dddd, J = 6.6, 4.4, 1.1, 1.1, 1H, CHOCO), 5.81
(ddd, J = 17.3, 10.5, 6.6, 1H, CH=CH2), 7.27–7.36
(m, 5H, ArH)
2c
2f
+ 5.1 (0.44,
CHCl3)
1.34–1.41 (m, 12H, CH3), 3.68 (t, J = 7.8, 1H, 25.18, 26.60, 26.91, 27.18 (4q, CH3), 42.99 (t,
CH2N), 3.93–4.24 (m, 6H, CH2N, CHO), 5.12 (s, CH2N), 67.13 (t, PhCH2), 67.66 (t, CH2O), 75.87,
2H, PhCH2), 5.29 (sbr, 1H, NH), 5.36–5.42 (m, 2H, 76.93, 78.55, 81.15 (4d, CHO), 109.93, 110.29 [2s,
CH=CH2), 5.52 (dd, J = 7.8, 3.2, 1H, CHOCO), 5.93 C(CH3)2], 121.45 (t, CH=CH2), 128.10, 128.52,
(ddd, J = 17.7, 8.9, 8.9, 1H, CH=CH2), 7.30–7.36 129.19 (3d, ArC), 131.07 (d, CH=CH2), 136.25 (s,
(m, 5H, ArH)
quart. ArC), 156.21 (s, OCON), 169.01 (s, COO)
+ 24.2 (2.5,
CHCl3)
0.88 (t, J = 7.0, 3H, CH2CH3), 1.25–1.33 (m, 4H, 13.96 (q, CH2CH3), 22.20 (t, CH2CH3), 25.40, 26.43
CH2), 1.34 [s, 3H, C(CH3)2], 1.39 [s, 3H, C(CH3)2], [2q, C(CH3)2], 30.99 (t, CH2), 32.12 (t, CH2), 43.14
2.05 (m, 2H, C = CHCH2), 3.77 (dd, J = 7.9, 6.8, 1H, (t, CH2N), 65.72 (t, CH2O), 67.25 (t, PhCH2), 75.54
CH2N), 3.91–4.13 (m, 4H, CH2O, CH2N, CHOC), (d, CHO), 76.83 (d, CHO), 110.06 [2s, C(CH3)2],
5.12 (s, 2H, PhCH2), 5.26 (mc, 1H, NH), 5.33–5.46 123.25 (d, CH=CHCH2), 128.22, 128.32, 128.66 (3d,
(m, 2H, CHOCH=CH, CHOCO), 5.81 (dt, J = 14.3, ArC), 136.42 (s, quart. ArC), 137.97 (d,
7.1, 1H, CH=CHCH2), 7.35 (m, 5H, ArH)
CHOCH=CH), 156.29 (s, OCON), 169.17 (s, COO)
2g
2h
– 40.3 (0.6,
CHCl3)
1.39 (d, J = 7.2, 1.5H, CH3), 1.47 (d, J = 7.2, 1.5H, 18.55, 18.77 (2q, CH3), 49.74 (d, CHN), 68.88 (t,
CH3), 4.47 (mc, 1H, CHN), 5.10 (s, 1H, PhCH2), 5.11 PhCH2), 72.21, 77.32 (2d, CHOCO), 117.41, 117.51
(s, 1H, PhCH2), 5.27 (m, 2H, CH=CHHt, NH), 5.34 (2t, CH=CH2), 126.95, 127.04, 128.05, 128.12,
(mc, 1H, CH=CHHc), 6.00 (ddd, J = 16.1, 10.7, 5.3, 128.31, 128.36, 128.49 (7d, ArC), 135.63 (d,
1H, CH=CH2), 6.28 (m, 1H, CHOCO), 7.34 (sbr, CH=CH2), 136.26, 138.14, 138.20 (3s, quart. ArC),
10H, ArH)
155.52 (s, OCON), 171.85 (s, COO)
– 26.0 (2.7,
CHCl3)
5.06 (d, J = 12.1, 1H, PhCH2), 5.12 (d, J = 12.1, 1H, 67.17 (t, PhCH2), 76.43, 77.85 (2d, CHN, CHOCO),
PhCH2), 5.26 (d, J = 10.4, 1H, CH=CHHt), 5.28 (d, J 117.9 (t, CH=CH2), 126.56, 127.31, 128.09, 128.20,
= 17.1, 1H, CH=CHHc), 5.46 (d, J = 7.5, 1H, CHN), 128.38, 128.55, 128.89 (7d, ArC), 135.58 (d,
5.83 (d, J = 7.3, 1H, NH), 5.97 (ddd, J = 17.0, 10.6, CH=CH2), 136.09, 136.36, 137.94 (3s, quart. ArC),
6.3, 1H, CH=CH2), 6.23 (d, J = 5.9, 1H, CHOCO), 155.33 (s, OCON), 169.67 (s, COO)
6.96 (d, J = 6.1, 2H, ArH), 7.28–7.38 (m, 13H, ArH)