C. Ohara et al. / Bioorg. Med. Chem. Lett. 18 (2008) 1810–1813
1813
In summary, we have achieved a highly feasible synthe-
sis of 3-hydroxypipecolic acid derivatives 1, 2, 3, 4 and
their enantiomers. Among the compounds obtained,
ata, H.; Feet, G. W. J. Tetrahedron: Asymmetry 2005, 16,
23; (d) Kato, A.; Kato, N.; Kano, E.; Adachi, I.; Ikeda,
K.; Yu, L.; Okamoto, T.; Banba, Y.; Ouchi, H.; Takahata,
H.; Asano, N. J. Med. Chem. 2005, 48, 2036; (e) Takahata,
H.; Banba, Y.; Ouchi, H.; Nemoto, H. Org. Lett. 2003, 5,
2
4
,5-dehydro-3-hydroxypipecolic acid 3 showed inhibi-
tory activity against b-N-acetylglucosaminidase. The re-
sult revealed that 3 may be a new lead compound for
designing novel inhibitors of b-N-acetylglucosamini-
dase, which would be a useful biological tool to investi-
gate the function of O-GlcNAc. It is also emphasized
that intermediate 10 will serve as a useful synthetic pre-
cursor for polyhydroxylated pipecolic acids. Study along
this line is ongoing, and the results, including results for
the synthesis of a 5-aza analogue of glucuronic acid, will
be reported elsewhere.
2
527; (f) Takahata, H.; Banba, Y.; Ouchi, H.; Nemoto, H.;
Kato, A.; Adachi, I. J. Org. Chem. 2003, 68, 3603; (g)
Mihara, Y.; Ojima, H.; Imahori, T.; Yoshimura, Y.;
Ouchi, H.; Takahata, H. Heterocycles 2007, 72, 633; (h)
Takahata, H.; Banba, Y.; Sasatani, M.; Ouchi, H.;
Nemoto, H.; Kato, A.; Adachi, I. Tetrahedron 2004, 60,
8199.
9
. Umezawa, H.; Aoyagi, T.; Komiyama, T.; Morishima, H.;
Hamada, M.; Takeuchi, T. J. Antibiot. 1974, 27, 963.
1
0. (a) Kim, I. S.; Oh, J. S.; Zee, O. K.; Jung, Y. H.
Tetrahedron 2007, 63, 2622; (b) Liang, N.; Datt, A. J. Org.
Chem. 2005, 70, 10182; (c) Kumar, P.; Bodas, M. S. J.
Org. Chem. 2005, 70, 360; (d) Ref. 7; (e) Scott, J. D.;
Williams, R. M. Tetrahedron Lett. 2000, 41, 8413; (f)
Jourdant, A.; Zhu, J. Tetrahedron Lett. 2000, 41, 7033; (g)
Battistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi,
G.; Fava, G. G.; Ferrari, M. B.; Casiraghi, G. Tetrahe-
dron: Asymmetry 1997, 8, 2975; (h) Makara, G. M.;
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Acknowledgments
This work was supported in part by a Grant-in-Aid for
Scientific Research (No. 18590012) and High Technol-
ogy Research Program from the Ministry of Education,
Sciences, Sports and Culture of Japan.
1
1
1. Simone, S.; Gunter, H. Eur. J. Org. Chem. 1999, 2515.
2. At this stage, a diastereomeric ratio was not determined.
References and notes
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