β-Amino-α-hydroxyacids (norstatines) are prepared from urethane N-protected carboxyanhydrides (UNCAs); the key step is the diastereoselective reduction of a keto-acetylenic compound, which lead is, with syn diastereoselectivity, to the corresponding propargylic alcohol.
References
1.
UmezawaH., AayagiT., MorishimaH., MatzuzakiM., HamadaM., and TakeuchiT., J. Antibiot., 1970, 23, 259.
2.
WilleyA., and RichD. H., Med. Res. Rev., 1993, 13, 327.
3.
(a) TamT. F., CarriereJ., McDonaldD., CastelhanoA. L., PliuraD. H., DewdneyN. J., ThomasE. M., BachC., BarnettJ., ChanH., and KrantzA., J. Med. Chem., 1992, 35, 1318; (b) N. Shibata, E. Itoh and S. Terashima, Chem. Pharm. Bull., 1998, 46, 733.
4.
IizukaK., KamijoT., KubotaT., AkahaneK., UmeyamaH., and KisoY., J. Med. Chem., 1988; 31, 702.
5.
FehrentzJ. A., CalifanoJ. C., AmblardM., LoffetA., and MartinezJ., Tetrahedron Lett., 1994, 35, 569.
