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
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.
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页码:1315 / 1326
页数:12
相关论文
共 22 条
[21]   BENZYLIDENE COMPOUNDS OF PENTONIC ACIDS AND PENTONIC ACID LACTONES [J].
ZINNER, H ;
VOIGT, H ;
VOIGT, J .
CARBOHYDRATE RESEARCH, 1968, 7 (01) :38-&
[22]  
IN PRESS TRENDS ORGA