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The spectral and analytical data of synthetic 1 are as follows: IR (neat): 3025, 2957, 2871, 2781, 1456, 1377, 1326, 1287, 1179,
913, 798, 715 cm-1. 1H NMR (500 MHz, CDCl3): δ = 0.93 (3 H, t, J = 7.5 Hz), 0.94 (3 H, d, J = 6.8 Hz), 1.25-1.34 (1 H, m), 1.35-1.41 (1 H, m), 1.42-1.52 (2 H, m), 1.61-1.67
(1 H, m), 1.68-1.75 (1 H, m), 1.76-1.83 (1 H, m), 1.84 (1 H, td, J = 9.1, 6.9 Hz), 1.99-2.07 (2 H, m), 2.08-2.14 (1 H, m), 2.64 (1 H, dtd, J = 11.0, 3.6, 1.9 Hz), 3.35 (1 H, td, J = 8.4, 1.9 Hz), 5.50 (1 H, dt, J = 10.2, 1.9 Hz), 5.57 (1 H, dt, J = 10.2, 1.9 Hz). 13C NMR (75 MHz, CDCl3): δ = 14.39 (q), 18.14 (q), 18.64 (t), 20.77 (t), 29.38 (t), 36.04 (t), 37.61 (d),
52.79 (t), 63.00 (d), 67.83 (d), 128.55 (d), 131.53 (d). HRMS: m/z calcd for C12H21N: 179.1674; found: 179.1686. [α]D
26 +129.3 (c 2.74, CHCl3).
<A NAME="RU09407ST-14">14</A>
The spectral and analytical data of synthetic 2 are as follows: IR (neat): 3030, 2957, 2929, 2871, 2781, 1458, 1378, 1329, 1260,
1177, 1105, 929, 803, 713 cm-1. 1H NMR (500 MHz, CDCl3): δ = 0.89 (3 H, t, J = 6.8 Hz), 0.91 (3 H, t, J = 7.3 Hz), 1.12-1.21 (1 H, m), 1.23-1.34 (2 H, m), 1.35-1.40 (2 H, m), 1.43-1.53
(3 H, m), 1.59-1.68 (1 H, m), 1.69-1.74 (1 H, m), 1.76-1.82 (1 H, m), 1.93 (1 H, td,
J = 9.4, 6.8 Hz), 1.99-2.06 (3 H, m), 2.63 (1 H, dtd, J = 11.0, 3.4, 1.7 Hz), 3.34 (1 H, td, J = 8.5, 2.1 Hz), 5.60 (1 H, dt, J = 9.8, 1.7 Hz), 5.63 (1 H, dt, J = 9.8, 1.7 Hz). 13C NMR (75 MHz, CDCl3): δ = 14.43 (2 × q), 18.64 (t), 19.67 (t), 20.92 (t), 29.69 (t), 34.91 (t), 36.11
(t), 42.54 (d), 52.76 (t), 62.97 (d), 66.13 (d), 129.01 (d), 129.44 (d). HRMS: m/z calcd for C14H25N 207.1986; found: 207.1973. [α]D
26 +109.1 (c 0.32, CHCl3). The GC-MS instrument is a Finnigan-Thermoquest Polaris Q with a Restek-RTX-5MS
column (30 m × 0.25 mm i.d.) and the program was 100-280 °C at 10 °C/min with a final
hold time of 10 min; t
R = 7.69 min.; natural product from Oophaga granulifera: t
R = 8.41 min. MS (EI): m/z (%) = 208 (12), 207 (4), 206 (8), 164 (100), 162 (13), 136 (13), 134 (13), 132 (8),
120 (52), 106 (8), 93 (22), 92 (11), 91 (10), 79 (13), 77 (16), 70 (16), 67 (24),
65 (14). MS (EI) of natural product from Dendrobates granuliferous: m/z (%) = 207 (2), 206 (4), 17 (10), 164 (100), 162 (78), 134 (18), 120 (28), 91 (12),
79 (14), 77 (20), 65 (11).
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Dani JA.
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