8824
7. (a) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl.
1994, 33, 1778; (b) Jespersen, T. M.; Bols, M.; Sierks, M. R.; Skrydstrup, T. Tetrahedron 1994, 50, 13449.
8. Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007.
9. Kim, Y. J.; Ichikawa, M.; Ichikawa, Y. J. Org. Chem. 2000, 65, 2599.
10. (a) Pandey, G.; Kumaraswamy, G.; Bhalerao, U. T. Tetrahedron Lett. 1989, 30, 6059; (b) Pandey, G.; Reddy, G.
D.; Kumaraswamy, G. Tetrahedron 1994, 50, 8185.
11. Yoshida, J.-i.; Maekawa, T.; Murata, T.; Matsunaga, S.-i.; Isoe, S. J. Am. Chem. Soc. 1990, 112, 1962.
12. Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337.
13. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972 3769.
1
14. Compound 7: H NMR (200 MHz, CDCl3) l 7.30 (m, 5H); 4.39 (dd, J=7.1, 2.0 Hz, 1H); 4.25 (m, 1H); 3.72 (d,
J=13.7 Hz, 1H); 3.49 (d, J=13.7 Hz, 1H); 2.67 (dd, J=13.1, 5.3 Hz, 1H); 2.57 (dd, J=13.1, 5.3 Hz, 1H); 2.50
(d, J=2.0 Hz, 1H); 2.16 (d, J=14.7 Hz, 1H); 2.02 (d, J=14.7 Hz, 1H); 1.47 (s, 3H); 1.37 (s, 3H); 0.05 (s, 9H);
13C NMR (75 MHz, CDCl3): l=139.6, 128.8, 128.0, 126.7, 110.2, 81.6, 80.7, 74.1, 68.8, 62.8, 58.4, 47.2, 26.9,
25.9, −1.33; IR (Neat) 3310 cm−1 (sharp); mass: m/z=331 (M+) (8%), 258 (10%), 206 (100%); [h]D20=+1.24
(c=21.2, CHCl3).
1
15. Compound 6: H NMR (200 MHz, CDCl3): l 7.30 (m, 5H); 5.05 (d, J=1.0 Hz, 1H); 4.90 (d, J=1.0 Hz, 1H);
3.80 (m, 1H); 3.73 (d, J=13.2 Hz, 1H); 3.65 (d, J=13.2 Hz, 1H); 3.57 (m, 1H); 3.33 (m, 2H); 2.80 (d, J=12.7
Hz, 1H); 2.37 (t, J=10.3 Hz, 1H); 1.45 (s, 6H); 13C NMR (50 MHz, CDCl3): l=140.4, 137.7, 128.8, 128.2, 127.1,
110.9, 105.1, 81.7, 77.5, 61.5, 57.1, 54.5, 26.8, 26.6; mass: m/z=259 (M+) (5%), 201 (67%), 91 (100%);
[h]2D0=−50.94 (c=1.9, CHCl3).
1
16. Compound 16: H NMR (200 MHz, CDCl3): l 7.30 (m, 5H); 3.70 (dd, J=10.3, 3.9 Hz, 1H); 3.65 (m, 4H); 3.24
(dd, 1H, J=9.3, 3.9 Hz, 1H); 3.15 (dd, J=10.7, 8.9 Hz, 1H); 2.95 (dd, J=11.3, 3.9 Hz, 1H); 2.18 (m, 2H); 1.95
(m, 1H); 1.45 (s, 6H); 13C NMR (75 MHz, CDCl3): l=129.0, 128.2, 127.3, 110.9, 82.1, 77.3, 63.5, 61.9, 54.3, 53.4,
41.5, 26.7; [h]2D0=+14.8 (c=0.5, MeOH).
1
17. Data for N-benzyl isofagomine: H NMR (200 MHz, D2O): l 7.30 (m, 5H); 3.73 (dd, J=11.3, 3.4 Hz, 1H); 3.55
(m, 4H); 3.15 (dd, J=10.2, 9.3 Hz, 1H); 2.95 (m, 2H); 1.95 (m, 2H); 1.70 (m, 1H); 13C NMR (75 MHz, D2O):
l=128.9, 127.1, 126.5, 72.4, 69.8, 60.0, 59.4, 55.5, 52.4, 41.3; [h]2D0=+12.65 (c=0.39, EtOH).
18. The characteristic data for 3 was in good agreement with that reported for its hydrochloride salt.7 1H NMR (300
MHz, D2O): l 3.76 (dd, J=11.4, 3.3 Hz, 1H); 3.59 (dd, J=11.5, 6.7 Hz, 1H); 3.48 (m, 1H); 3.27 (dd, J=10.6,
8.8 Hz, 1H); 3.12 (m, 2H); 2.43 (m, 2H); 1.70 (m, 1H); 13C NMR (75 MHz, D2O): l=70.2, 68.4, 57.1, 45.9, 42.9,
41.0; mass: m/z=147 (M+) (44%), 129 (42%), 112 (62%), 98 (100%); [h]2D0=+16.25 (c=0.32, EtOH). 3·HCl:
[h]2D0=+20.72 (c=0.4, EtOH); Lit7: [h]D20=+19.6 (c=0.85, EtOH). For (−)-isofagomine: [h]2D0=−15.78 (c=0.19,
EtOH); 17·HCl: [h]D20=−20.25 (c=0.31, EtOH).
.