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H. Ohno et al.
LETTER
(16) (a) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.;
Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 1159.
(b) Ohno, H.; Tanaka, H.; Takahashi, T. Synlett 2004, 508.
(17) The lower yield than previously reported16a was due to the
different ways of estimation of the yield. The yield was
determined by measurement of mass weight of cleavage
product in the former paper, on the other hand in this paper
the yield is isolated yield.
132.1, 140.1, 140.8, 144.3, 144.8, 145.1. MS (ESI): 527 [M
+ H]+.
Spectra of 8g: 1H NMR (400 MHz, CD3OD): d = 0.15–0.24
(2 H, m), 0.52–0.61 (2 H, m), 0.94 (1 H, m), 1.73 (1 H, m),
1.81–1.91 (4 H, m), 2.31–2.49 (4 H, m), 2.59 (1 H, d,
J = 15.9 Hz), 2.75–2.87 (7 H, m), 3.17 (1 H, d, J = 18.6 Hz),
3.41 (1 H, d, J = 5.9 Hz), 5.60 (1 H, s), 6.52 (1 H, d, J = 8.2
Hz), 6.54 (1 H, d, J = 8.2 Hz), 6.67 (1 H, d, J = 8.1 Hz), 7.10
(1 H, d, J = 8.1 Hz). 13C NMR (150.8 MHz, CD3OD): d =
4.2, 4.8, 10.2, 24.2, 24.2, 24.9, 25.4, 30.0, 30.6, 32.7, 45.0,
49.9, 60.4, 63.5, 74.4, 86.3, 116.7, 118.1, 119.4, 120.4,
121.5, 125.3, 125.9, 129.5, 131.3, 132.1, 137.7, 140.8,
144.5, 150.4. MS (ESI): 469 [M + H]+.
(18) Spectra of 8d: 1H NMR (400 MHz, CD3OD): d = 0.13–0.23
(2 H, m), 0.52–0.61 (2 H, m), 0.93 (1 H, m), 1.30 (3 H, t,
J = 7.6 Hz), 1.72 (1 H, d, J = 12.2 Hz), 2.28–2.50 (4 H, m),
2.56 (1 H, d, J = 15.9 Hz), 2.73 (1 H, d, J = 15.9 Hz), 2.73–
2.90 (4 H, m), 3.17 (1 H, d, J = 18.6 Hz), 3.40 (1 H, d, J = 6.3
Hz), 5.59 (1 H, s), 6.53 (1 H, d, J = 8.1 Hz), 6.56 (1 H, d,
J = 8.1 Hz), 7.00 (1 H, d, J = 1.7 Hz), 7.34 (1 H, d, J = 1.7
Hz). 13C NMR (150.8 MHz, CD3OD): d = 4.2, 4.8, 10.3,
14.6, 24.1, 25.1, 29.8, 32.8, 45.0, 60.4, 63.4, 74.4, 85.7,
111.1, 113.0, 118.2, 119.6, 119.7, 124.4, 126.0, 129.3,
130.2, 131.8, 131.9, 135.8, 140.8, 144.5. MS (ESI): 521 [M
+ H]+.
Spectra of 8h: 1H NMR (400 MHz, CD3OD): d = 0.12–0.22
(2 H, m), 0.49–0.60 (2 H, m), 0.92 (1 H, m), 1.75 (1 H, d,
J = 12.7 Hz), 2.27–2.46 (4 H, m), 2.66 (1 H, d, J = 15.6 Hz),
2.71–2.76 (1 H, m), 2.83 (1 H, d, J = 18.6 Hz), 2.84 (1 H, d,
J = 15.9 Hz), 3.17 (1 H, d, J = 18.6 Hz), 3.42 (1 H, d, J = 6.3
Hz), 5.68 (1 H, s), 6.54 (1 H, d, J = 8.2 Hz), 6.57 (1 H, d,
J = 8.2 Hz), 7.45–7.49 (1 H, m), 7.51–7.55 (1 H, m), 7.58 (1
H, s), 8.19–8.23 (2 H, m). 13C NMR (150.8 MHz, CD3OD):
d = 4.2, 4.7, 10.2, 24.1, 29.7, 32.7, 44.8, 60.3, 63.3, 74.4,
85.7, 112.6, 118.0, 119.5, 119.7, 121.7, 122.8, 123.5, 123.9,
125.3, 125.8, 125.9, 126.8, 128.2, 129.9, 131.7, 132.3,
140.6, 144.4. MS (ESI): 499 [M + H]+.
Spectra of 8e: 1H NMR (400 MHz, CD3OD): d = 0.13–0.22
(2 H, m), 0.51–0.60 (2 H, m), 0.93 (1 H, m), 1.73 (1 H, d,
J = 12.5 Hz), 2.28–2.47 (4 H, m), 2.49 (3 H, s), 2.57 (1 H, d,
J = 15.9 Hz), 2.68–2.85 (2 H, m), 2.76 (1 H, d, J = 15.9 Hz),
3.17 (1 H, d, J = 18.6 Hz), 3.40 (1 H, d, J = 6.3 Hz), 5.59 (1
H, s), 6.52 (1 H, d, J = 8.1 Hz), 6.55 (1 H, d, J = 8.1 Hz), 6.90
(1 H, d, J = 8.4 Hz), 7.16 (1 H, d, J = 8.4 Hz). 13C NMR
(150.8 MHz, CD3OD): d = 4.2, 4.8, 10.3, 14.1, 24.1, 29.8,
32.7, 45.0, 60.4, 63.5, 74.4, 85.8, 111.8, 117.8, 118.2, 119.3,
119.6, 120.9, 125.9, 126.2, 128.4, 131.5, 131.9, 138.5,
140.8, 144.5. MS (ESI): 463 [M + H]+.
Spectra of 8i: 1H NMR (400 MHz, CD3OD): d = 0.12–0.24
(2 H, m), 0.51–0.62 (2 H, m), 0.87–0.97 (1 H, m), 1.73–1.76
(1 H, m), 2.28–2.50 (4 H, m), 2.63 (1 H, d, J = 14.6 Hz),
2.72–2.88 (2 H, m), 2.81 (1 H, d, J = 15.6 Hz), 3.18 (1 H, d,
J = 18.6 Hz), 3.42 (1 H, d, J = 6.6 Hz), 3.81 (1 H, d, J = 22.0
Hz), 3.90 (1 H, d, J = 21.7 Hz), 5.63 (1 H, s), 6.54 (1 H, d,
J = 8.1 Hz), 6.56 (1 H, d, J = 8.1 Hz), 7.15–7.19 (1 H, m),
7.26–7.30 (1 H, m), 7.31 (1 H, d, J = 8.1 Hz), 7.41 (1 H, d,
J = 8.3 Hz), 7.46 (1 H, d, J = 7.3 Hz), 7.68 (1 H, d, J = 7.6
Hz). 13C NMR (150.8 MHz, CD3OD): d = 4.2, 4.8, 10.3,
24.2, 30.1, 32.7, 35.2, 45.0, 60.4, 63.5, 74.4, 86.1, 112.2,
112.4, 118.2, 118.5, 119.6, 119.8, 125.6, 126.0, 126.1,
126.5, 127.4, 127.6, 131.0, 132.1, 135.5, 137.8, 140.9,
143.5, 144.4, 144.6. MS (ESI): 503 [M + H]+.
Spectra of 8f: 1H NMR (400 MHz, CD3OD): d = 0.15–0.24
(2 H, m), 0.52–0.62 (2 H, m), 0.95 (1 H, m), 1.26–1.42 (18
H, m), 1.74 (1 H, m), 2.35–2.49 (4 H, m), 2.71–2.81 (3 H,
m), 3.18–3.26 (2 H, m), 3.36 (1 H, d, J = 6.3 Hz), 5.61 (1 H,
s), 6.53 (1 H, d, J = 8.2 Hz), 6.56 (1 H, d, J = 8.2 Hz), 7.05
(1 H, d, J = 1.7 Hz), 7.20 (1 H, d, J = 1.7 Hz). 13C NMR
(150.8 MHz, CD3OD): d = 4.3, 4.7, 10.3, 24.2, 31.9, 32.2,
33.0, 35.6, 36.3, 36.5, 44.9, 48.0, 60.5, 63.9, 75.0, 86.6,
107.0, 108.9, 115.2, 118.2, 119.5, 122.6, 125.9, 130.9,
Synlett 2005, No. 7, 1191–1194 © Thieme Stuttgart · New York