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4. For recent references on the syntheses of 2-hydroxy-
methylpiperidin-3-ol, see: (a) Takahata, H.; Banda, Y.;
Sasatani, M.; Nemoto, H.; Kato, A.; Adachi, I. Tetrahe-
dron 2004, 60, 8199; (b) Takahata, H.; Banda, Y.; Ouchi,
H.; Nemoto, H.; Kato, A.; Adachi, I. J. Org. Chem. 2003,
68, 3603; (c) Haukaas, M. H.; O’Doherty, G. A. Org. Lett.
2001, 3, 401.
5. For recent references on the syntheses of febrifugine and/or
isofebrifugine, see: (a) Ashoorzadeh, A.; Caprio, V. Synlett
2005, 346; (b) Katoh, M.; Matsune, R.; Nagase, H.;
Honda, T. Tetrahedron Lett. 2004, 45, 6221; (c) Huang,
P.-Q.; Wei, B.-G.; Ruan, Y.-P. Synlett 2003, 1663; (d)
Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S.
J. Am. Chem. Soc. 2001, 123, 12510; (e) Sugiura, M.; Hagio,
H.; Hirabayashi, R.; Kobayashi, S. J. Org. Chem. 2001, 66,
809; (f) Sugiura, M.; Kobayashi, S. Org. Lett. 2001, 3, 477;
(g) Ooi, H.; Urushibara, A.; Esumi, T.; Iwabuchi, Y.;
Hatakeyama, S. Org. Lett. 2001, 3, 953; (h) Takeuchi, T.;
Azuma, K.; Takakura, K.; Abe, H.; Kim, H.-S.; Wataya,
Y.; Harayama, T. Tetrahedron 2001, 57, 1213; (i) Takeuchi,
T.; Ogasawara, K. Org. Lett. 2000, 2, 3193; (j) Okitsu, O.;
Suzuki, R.; Kobayashi, S. Synlett 2000, 989.
6. For recent references on the syntheses of prosophylline
and/or deoxoprosophylline, see: (a) Lee, H. K.; Chun, J.
S.; Pak, C. S. Tetrahedron 2003, 59, 6445; (b) Cossy, J.;
Willis, C.; Bellosta, V.; BouzBouz, S. J. Org. Chem. 2002,
67, 1982; (c) Koulocheri, S. D.; Magiatis, P.; Haroutou-
nian, S. A. J. Org. Chem. 2001, 66, 7915; (d) Datta, A.;
Kumar, J. S. R.; Roy, S. Tetrahedron 2001, 57, 1169.
7. (a) Kim, I. S.; Zee, O. P.; Jung, Y. H. Org. Lett. 2006, 8, in
press; (b) Kim, I. S.; Kim, J. D.; Ryu, C. B.; Zee, O. P.;
Jung, Y. H. Tetrahedron 2006, 62, in press; (c) Kim, J. D.;
Kim, I. S.; Jin, C. H.; Zee, O. P.; Jung, Y. H. Org. Lett.
2005, 7, 4025; (d) Kim, J. D.; Kim, I. S.; Hua, J. C.; Zee,
O. P.; Jung, Y. H. Tetrahedron Lett. 2005, 46, 1079; (e)
Kim, J. D.; Zee, O. P.; Jung, Y. H. J. Org. Chem. 2003, 68,
3721; (f) Kim, J. D.; Han, G.; Jeong, L. S.; Park, H.-J.;
Zee, O. P.; Jung, Y. H. Tetrahedron 2002, 58, 4395; (g)
Kim, J. D.; Lee, M. H.; Han, G.; Park, H.; Zee, O. P.;
Jung, Y. H. Tetrahedron 2001, 57, 8257; (h) Kim, J. D.;
Lee, M. H.; Lee, M. J.; Jung, Y. H. Tetrahedron Lett.
2000, 41, 5073.
8. (a) Allred, E. L.; Winstein, S. J. Am. Chem. Soc. 1967, 89,
3991; (b) Allred, E. L.; Winstein, S. J. Am. Chem. Soc.
1967, 89, 3998; (c) Krow, G. R.; Yuan, J.; Lin, G.; Sonnet,
P. E. Org. Lett. 2002, 4, 1259; (d) Roberts, D. D. J. Org.
Chem. 1997, 62, 1857.
9. (a) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless,
K. A. J. Org. Chem. 1981, 46, 3936; (b) Nunez, M. T.;
Martin, V. S. J. Org. Chem. 1990, 55, 1928.
10. (a) Schuda, P. F.; Cichowicz, M. B.; Heiman, M. R.
Tetrahedron Lett. 1983, 24, 3829; (b) Chaudhuri, S. R.;
Gurjar, M. K. Tetrahedron Lett. 2002, 43, 2435.
11. Analytical data for 1: Rf = 0.32 (EtOAc/MeOH/30%
25
NH4OH 5:5:1); mp 229–235 °C (decomp); ½aꢁD +13.0 (c
0.5, 10% HCl); 1H NMR (500 MHz, D2O) d 1.59–1.67 (m,
2H, H-4ax and H-5ax), 1.84–1.95 (m, 2H, H-4eq and H-5eq),
3.02 (ddd, 1H, J = 11.0, 7.0, 2.5 Hz, H-6ax), 3.25–3.30 (m,
1H, H-6eq), 3.53 (d, 1H, J = 6.5 Hz, H-2), 4.05–4.08 (br,
1H, H-3); 13C NMR (125 MHz, D2O) d 18.50, 28.32,
42.60, 62.10, 66.04, 172.12; HRMS (CI) Calcd for
C6H12NO3 [M+H+] 146.0817, found 146.0817.
12. Analytical data for 2: Rf = 0.20 (CHCl3/MeOH 5:1); mp
25
155 °C (decomp); ½aꢁD +55.0 (c 0.1, MeOH); 1H NMR
(500 MHz, D2O) d 1.53–1.60 (m, 1H), 1.71–1.76 (m, 1H),
1.99 (dt, 1H, J = 14.5, 3.5 Hz), 2.14–2.19 (m, 1H), 2.93 (dt,
1H, J = 13.0, 3.5 Hz), 2.98 (ddd, 1H, J = 9.5, 6.5, 3.5 Hz),
3.33 (br dd, 1H, J = 13.0, 3.5 Hz), 3.74 (dt, 1H, J = 9.5,
4.5 Hz), 3.85 (dd, 1H, J = 12.5, 6.5 Hz), 3.98 (dd, 1H,
J = 12.5, 3.5 Hz); 13C NMR (125 MHz, D2O) d 21.22,
31.01, 43.90, 58.97, 61.97, 65.48; HRMS (CI) Calcd for
C6H14NO2 [M+H+] 132.1024, found 132.1024.