A stereoselective total synthesis of (2R,3S)-3-hydroxypipecolic acid starting from an enantiomerically pure α-amino alcohol is reported. The synthesis involved a regioselective mesylation and subsequent cyclisation as key steps.
(a) DragovichP.S., ParkerJ.E., IncacuanM., KalishV.J., KissingerC.R., KnightonD.R., LewisC.T., MoomawE.W., PargeH.E., PelletierL.A.K., PrinsT.J., ShowalterR.E., TatlockJ.H., TuckerK.D., and VillafrancaJ.E., J. Med. Chem., 1996, 39, 1872; (b) M.W. Harding, A. Galat, D.E. Uehling and S.L. Schreiber, Nature, 1989, 341, 758.
6.
(a) ShilvockJ.P., NashR.J., LloydJ.D., WintersA.L., AsanoN., and FleetG.W.J., Tetrahedron: Asymmetry, 1998, 9, 3505; (b) B. Ho and T.M. Zabriskie, Bioorg. Med. Chem. Lett., 1998, 8, 739.
7.
(a) NinomiyaI., KiguchiT., and NaitoT., Alkaloids, 1998, 50, 317; (b) A.J. Freyer, A.D. Patil, L. Killmer, N. Troupe, M. Mentzer, B. Carte, L. Faucette and R.K. Johnson, J. Nat. Prod., 1997, 60, 896; (c) T. Sato, F. Hirayama and T. Saito, J. Antibiot. 1991, 44, 1367; (d) K. Suzuki, T. Sato, M. Morika, K. Nagai, A. Kenji, H. Yamaguchi and T. Saito, J. Antibiot., 1991, 44, 479.
8.
(a) LamarreD., CroteauG., BourgonL., ThibeultD., WardropE., ClouetteC., VaillancourtM., CohenE., PargellisC., YoakimC., and AndersonP.C., Antimicrob. Agents Chemother., 1997, 41, 965; (b) P.C. Anderson, F. Soucy, C. Yoakim, P. Lavallée and P.L. Beaulieu, US Patent, 5545640, 1996.
9.
(a) LiangN., and DattaA., J. Org. Chem., 2005, 70, 10182; (b) P. Kumar and M.S. Bodas, J. Org. Chem., 2005, 70, 360; (c) M. S. Bodas and P. Kumar, Tetrahedron Lett., 2004, 45, 8461; (d) S.D. Koulocheri, P. Magiatis, A.-L. Skaltsounis and S.A. Haroutounian, Tetrahedron, 2002, 58, 6665; (e) M. Haddad and M. Larcheveque, Tetrahedron Lett., 2001, 42, 5223; (f) A. Jourdant and J. Zhu, Tetrahedron Lett., 2000, 41, 7033; (g) M. Horikawa, J. Busch-Petersen and E.J. Corey, Tetrahedron Lett., 1999, 40, 3843; (h) C.H. Sugisaki, P.J. Carroll and C.R.D. Correia, Tetrahedron Lett., 1998, 39, 3413; (i) L. Battistini, F. Zanardi, G. Rassu, P. Spanu, G. Pelosi, G.G. Fava, M.B. Ferrari and G. Casiraghi, Tetrahedron: Asymmetry, 1997, 8, 2975; (j) C. Agami, F. Couty and H. Mathieu, Tetrahedron Lett., 1996, 37, 4001.
10.
HaddadM., LarchevêqueM., and TongH. M., Tetrahedron Lett., 2005, 46, 6015.
11.
GrykoD., ProkopowiczP., and JurczakJ., Tetrahedron: Asymmetry, 2002, 13, 1103.
12.
CarlsenP.H.J., KatsukiT., MartinV.S., and SharplessK.B., J. Org. Chem., 1981, 46, 3936.
