STEREOSELECTIVE SYNTHESIS OF 4,5-DIHYDROXY-D-ERYTHRO-NORVALINE AND 4,5-DIHYDROXY-D-THREO-L-NORVALINE FROM D-RIBONOLACTONE

被引：17

作者：

ARIZA, J ^{[1
]}

DIAZ, M ^{[1
]}

FONT, J ^{[1
]}

ORTUNO, RM ^{[1
]}

机构：

[1] UNIV AUTONOMA BARCELONA,DEPT QUIM,E-08193 BARCELONA,SPAIN

来源：

TETRAHEDRON | 1993年 / 49卷 / 06期

关键词：

D O I：

10.1016/S0040-4020(01)85821-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrogen functions have been introduced stereoselectively at the C-2 position in D-ribonolactone derivatives in order to prepare the title unnatural amino acids. The synthetic strategies lie in the inversion of configuration in S(N)2-type substitution reactions and stereospecific hydrogenation of conveniently substituted butenolides. The threo-isomer is the key precursor in the synthesis of the antibiotic clavalanine.

引用

页码：1315 / 1326

页数：12