MS (ESI) m/z 454 [M + NH4+]. Anal. Calcd for C21H24O8S: C,
57.79; H, 5.54. Found: C, 57.77; H: 5.82.
Compound 18. This compound was prepared from 4, yielding
18 by column chromatography (petroleum ether/ethyl acetate
10:1): 1H NMR (CDCl3, 500 MHz) δ 2.13 (s, 3H), 2.62 (br, 1H),
3.51-3.58 (m, 2H), 3.59 (s, 3H), 3.64 (t, 1H, J ) 9.5 Hz), 3.79 (t,
1H, J ) 10.0 Hz), 4.37 (dd, 1H, J ) 5.0, 10.0 Hz), 4.38 (d, 1H, J
) 7.5 Hz), 5.22 (t, 1H, J ) 9.5 Hz), 5.50 (s, 1H), 7.35-7.38 (m,
3H), 7.44-7.46 (m, 2H); 13C NMR (CDCl3, 125 MHz) δ 20.97,
57.62, 66.46, 68.61, 73.44, 73.58, 78.46, 101.49, 104.52, 126.12,
128.23, 129.09, 136.88, 171.03; MS (ESI) m/z 342 [M + NH4+].
Anal. Calcd for C16H20O7: C, 59.25; H, 6.22. Found: C, 59.37;
H, 6.09.
Compound 12. This compound was prepared from 5, yielding
12 by column chromatography (petroleum ether/ethyl acetate
6:1): 1H NMR (CDCl3, 300 MHz) δ 7.75 (d, 2H, J ) 8.1 Hz),
7.71-7.36 (m, 7H), 5.27 (s, 1H), 4.50 (dd, 1H, J ) 3.6 Hz, J )
9.6 Hz), 4.20-4.25 (m, 2H), 4.14 (d, 1H, J ) 7.8 Hz), 3.84-3.96
(m, 2H), 3.46 (s, 3H), 3.37 (s, 1H), 2.34 (d, 1H, J ) 2.7 Hz), 2.31
(s, 3H); 13C NMR (CDCl3, 75 MHz) δ 21.63, 57.24, 66.06, 68.36,
68.76, 74.09, 80.35, 100.84, 103.60, 126.14, 127.84, 128.00,
128.93, 129.63, 133.80, 137.20, 144.90; MS (ESI) m/z 454 [M +
NH4+]. Anal. Calcd for C21H24O8S: C, 57.79; H, 5.54. Found: C,
57.68; H, 5.68.
Compound 13. This compound was prepared from 6, yielding
13 by column chromatography (petroleum ether/ethyl acetate
5:1): 1H NMR (CDCl3, 500 MHz) δ 2.41 (s, 3H), 3.44 (s, 3H),
3.67 (br s, 1H), 4.04 (d, 1H, J ) 1.5 Hz), 4.15 (dd, 1H, J ) 3.5,
9.5 Hz), 4.25-4.27 (m, 1H), 4.36 (d, 1H, J ) 3.5 Hz), 4.82 (dd,
1H, J ) 3.5, 9.5 Hz), 4.90 (d, 1H, J ) 3.5 Hz), 5.39 (s, 1H), 7.28-
7.46 (m, 7H), 7.84 (d, 2H J ) 8.5 Hz); 13C NMR (CDCl3, 75 MHz)
δ 21.65, 55.73, 62.44, 66.32, 68.92, 74.76, 78.65, 100.17, 100.65,
126.05, 127.80, 128.07, 128.96, 129.67, 133.97, 137.23, 144.84;
MS (ESI) m/z 454 [M + NH4+].
Compound 19. This compound was prepared from 5, yielding
19 by column chromatography (petroleum ether/ethyl acetate
8:1): 1H NMR (CDCl3, 300 MHz) δ 2.14 (s, 3H), 2.43 (br., 1H),
3.51 (d, 1H, J ) 1.5 Hz), 3.59 (s, 3H), 4.01 (dd, 1H, J ) 7.5, 10.0
Hz), 4.07 (dd, 1H, J ) 1.5, 7.5 Hz), 4.29 (d, 1H, J ) 7.5 Hz),
4.34 (dd, 1H, J ) 1.5, 12.5 Hz), 4.40 (dd, 1H, J ) 1.0, 3.5 Hz),
4.86 (dd, 1H, J ) 3.5, 10.0 Hz), 5.50 (s, 1H), 7.33-7.38 (m, 3H),
7.48-7.51 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 57.24, 66.44,
68.50, 68.99, 73.28, 73.79, 100.89, 103.99, 126.24, 128.10, 128.97,
137.54, 171.04; MS (ESI) m/z 342 [M + NH4+]. Anal. Calcd for
C
16H20O7: C, 59.25; H, 6.22. Found: C, 59.03; H, 6.42.
Compound 20. This compound was prepared from 6, yielding
Compound 14. This compound was prepared from 7, yielding
14 by column chromatography (petroleum ether/ethyl acetate
8:1 containing 2% of Et3N): 1H NMR (CDCl3, 500 MHz) δ 2.36
(s, 3H), 2.37 (s, 3H), 2.78 (br s, 1H), 3.82 (t, 1H, J ) 10.5 Hz),
4.16 (t, 1H, J ) 9.5 Hz), 4.18 (dd, 1H, J ) 5.0, 10.5 Hz), 4.32
(td, 1H, J ) 5.0, 10.5 Hz), 4.59 (br s, 1H), 4.84 (dd, 1H, J ) 3.5,
10.0 Hz), 5.44 (s, 1H), 5.52 (s, 1H), 7.11 (d, 2H, J ) 8.0 Hz),
7.16 (d, 2H, J ) 8.0 Hz), 7.27 (d, 2H, J ) 8.0 Hz), 7.34-7.40 (m,
5H), 7.78 (d, 2H, J ) 8.0 Hz); MS (ESI) m/z 546 [M + NH4+].
Compound 15. This compound was prepared from 1, yielding
15 by column chromatography (petroleum ether/ethyl acetate
8:1): 1H NMR (CDCl3, 300 MHz) δ 7.47∼7.29 (m, 5H), 5.50 (s,
1H), 5.33 (t, 1H, J ) 9.6 Hz), 4.81 (d, 1H, J ) 4.2 Hz), 4.30 (dd,
1H, J ) 4.5, 9.3 Hz), 3.63-3.91 (m, 3H), 3.59 (t, 1H, J ) 9.6
Hz), 3.43 (s, 3H), 2.25 (s, 3H); MS (FAB) m/z 325 [M + H+]. Anal.
Calcd for C16H20O7: C, 59.25; H, 6.22. Found: C, 59.09; H, 6.20.
Compound 16. This compound was prepared from 2, yielding
16 by column chromatography (petroleum ether/ethyl acetate
10:1): 1H NMR (CDCl3, 300 MHz) δ 7.57 (d, 2H, J ) 7.8 Hz),
7.29-7.40 (m, 5H), 7.07 (d, 2H, J ) 7.8 Hz), 5.46 (s, 1H), 4.90
(dd, 1H, J ) 3.3, 12.0 Hz), 4.55 (d, 1H, J ) 9.3 Hz), 4.37 (m,
2H), 4.02 (dd, 1H, J ) 1.5, 12.0 Hz), 3.90 (t, 1H, J ) 9.6 Hz),
3.60 (s, 1H), 2.60 (br, 1H), 2.34 (s, 3H), 2.13 (s, 3H); MS (FAB)
m/z 455 [M + K+]. Anal. Calcd for C22H24O6S: C, 63.44; H, 5.81.
Found: C, 63.69; H, 5.82.
20 by column chromatography (petroleum ether/ethyl acetate
6:1): 1H NMR (CDCl3, 300 MHz) δ 2.15 (s, 3H), 2.40 (d, 1H, J )
10.5 Hz), 3.40 (s, 3H), 3.74 (br s, 1H), 4.07-4.12 (m, 2H), 4.28-
4.32 (m, 2H), 4.98 (d, 1H, J ) 3.6 Hz), 5.16 (dd, 1H, J ) 3.6 Hz,
J ) 10.2 Hz), 5.57 (s, 1H), 7.37-7.40 (m, 3H), 7.50-7.52 (m,
2H); 13C NMR (CDCl3, 75 MHz) δ 21.05, 45.72, 55.53, 62.32,
67.15, 69.13, 71.19, 98.11, 101.35, 126.28, 128.26, 129.26, 137.30,
171.04; MS (ESI) m/z 342 [M + NH4+].
Compound 21. This compound was prepared from 7, yielding
21 by column chromatography (petroleum ether/ethyl acetate
6:1): 1H NMR (CDCl3, 500 MHz) δ 2.16 (s, 3H), 2.33 (s, 3H),
2.42 (br s, 1H), 3.84 (t, 1H, J ) 10.0 Hz), 3.98 (t, 1H, J ) 10.0
Hz), 4.24 (d, 1H, J ) 5.0 Hz), 4.25 (d, 1H, J ) 5.0 Hz), 4.38 (dt,
1H, J ) 5.0, 10.0 Hz), 5.40 (br s, 1H), 5.48 (dd, 1H, J ) 1.0, 3.0
Hz), 5.62 (s, 1H), 7.13 (d, 2H, J ) 8.0 Hz), 7.36 (d, 2H, J ) 8.0
Hz), 7.38-7.39 (m, 3H), 7.51-7.53 (m, 2H); 13C NMR (CDCl3,
125 MHz) δ 20.97, 21.12, 64.5, 67.74, 68.40, 73.54, 79.14, 87.25,
102.24, 126.25, 128.37, 129.21, 129.32, 129.98, 132.71, 137.01,
138.38, 170.35; MS (ESI) m/z 434 [M + NH4+].
Ack n ow led gm en t. This work was financially sup-
ported by the National Natural Science Foundation of
China. J .S. is on study leave from Guangdong Medical
College, Zhanjiang, China.
Compound 17. This compound was prepared from 3, yielding
17 by column chromatography (petroleum ether/ethyl acetate
8:1): 1H NMR (CDCl3, 500 MHz) δ 7.43-7.48 (m, 2H), 7.34-7.39
(m, 5H), 7.13 (d, 2H, J ) 7.5 Hz), 5.53 (s, 1H), 4.91 (dd, 1H, J )
9.0, 10.0 Hz), 4.67 (d, 1H, J ) 10.0 Hz), 4.38 (dd, 1H, J ) 5.0,
10.5 Hz), 3.91 (dt, 1H, J ) 3.5, 9.0 Hz), 3.78 (t, 1H, J ) 10.0 Hz),
3.54 (t, 1H, J ) 9.0 Hz), 3.46∼3.51 (m, 1H), 2.49 (d, 1H, J ) 3.0
Hz), 2.35 (s, 3H), 2.19 (s, 3H); MS (FAB) m/z 416 [M+]. Anal.
Calcd for C22H24O6S: C, 63.44; H, 5.81. Found: C, 63.07; H, 5.74.
Su p p or tin g In for m a tion Ava ila ble: Experimental pro-
cedures and characterization data for compounds 22-27.
Selected 1H NMR, 13C NMR, and 2D NMR spectra for
compounds 8-27. This material is available free of charge via
the Internet at http://pubs.acs.org.
J O0497252
J . Org. Chem, Vol. 69, No. 17, 2004 5777