Amberlite XAD-4 column (5 g), which was prepared as described
above. The column was washed with water (100 cm3) and then
with 25% CH3CN (50 cm3) and eluted with 80% CH3CN (50 cm3).
The fraction was evaporated to give 3 as a white solid in almost
quantitative recovery yield. m/z (SIMS, positive) MH+, 407.1302.
C20H23NO9 requires m/z 407.1321; dH (400 MHz, CD3OD) 1.56
(3H, d, J 7.2, CHCH3), 3.30–3.50 (3H, m, C2-, C3- and C4-H), 3.84
(1H, d, J 8.8, C5-H), 3.88 (3H, s, ArOCH3), 3.97 (1H, q, J 7.2,
CHCH3), 5.53 (1H, d, J 8.1, C1-H), 7.09 (1H, dd, J 2.4 and 8.9,
Ar-H), 7.18 (1H, s, Ar-H), 7.39 (1H, dd, J 1.7 and 8.5, Ar-H) and
7.67–7.72 (3H, m, Ar-H); dC (100 MHz, CD3OD) 19.23, 46.46,
55.72, 73.02, 73.60, 77.27, 77.60, 95.82, 106.54, 119.88, 127.14,
127.29, 128.26, 130.29, 130.41, 135.27, 136.58, 159.17, 172.87 and
174.92.
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