Stereocontrol in the addition of allyl metal reagents to an optically active imine derived from malic acid, leading to a formal synthesis of (+)-negamycin

被引:14
作者
Shimizu, M [1 ]
Morita, A [1 ]
Fujisawa, T [1 ]
机构
[1] Mie Univ, Dept Chem Mat, Tsu, Mie 5148507, Japan
关键词
D O I
10.1246/cl.1998.467
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Complete anti-stereoselection has been achieved on the addition of allyl metal reagents to an optically active imine derived from malic acid. The homoallyl amine thus obtained was converted into the known intermediate for the synthesis of (+)-Negamycin in enantiomerically pure form.
引用
收藏
页码:467 / 468
页数:2
相关论文
共 23 条
[11]  
MUKAIYAMA T, 1983, CHEM LETT, P971
[12]   STEREOCONTROLLED SYNTHESIS OF (+)-NEGAMYCIN BY 1,3-ASYMMETRIC INDUCTION [J].
OHNO, M ;
KOBAYASHI, S ;
IZAWA, T ;
WANG, YF .
NIPPON KAGAKU KAISHI, 1983, (09) :1299-1307
[13]   SYNTHESIS OF (+/-)-NEGAMYCIN AND OF (+/-)-EPINEGAMYCIN [J].
PASQUET, G ;
BOUCHEROT, D ;
PILGRIM, WR ;
WRIGHT, B .
TETRAHEDRON LETTERS, 1980, 21 (10) :931-934
[14]  
REETZ MT, 1994, ORGANOMETALLICS SYNT, P198
[15]   COMBINATION OF BORANE-DIMETHYL SULFIDE COMPLEX WITH CATALYTIC SODIUM TETRAHYDROBORATE AS A SELECTIVE REDUCING AGENT FOR ALPHA-HYDROXY ESTERS, VERSATILE CHIRAL BUILDING BLOCK FROM (S)-(-)-MALIC ACID [J].
SAITO, S ;
HASEGAWA, T ;
INABA, M ;
NISHIDA, R ;
FUJII, T ;
NOMIZU, S ;
MORIWAKE, T .
CHEMISTRY LETTERS, 1984, (08) :1389-1392
[16]  
SCHMIDT U, 1992, SYNTHESIS-STUTTGART, P482
[17]  
SHIBAHARA S, 1972, J AM CHEM SOC, V94, P4953
[18]   Stereocontrol in the addition of nucleophiles to an optically active aldehyde derived from L-serine, leading to a short-step synthesis of (2S,3S,4R)-phytosphingosine [J].
Shimizu, M ;
Wakioka, I ;
Fujisawa, T .
TETRAHEDRON LETTERS, 1997, 38 (34) :6027-6030
[19]  
STREICHER W, 1982, J ANTIBIOT, V31, P725
[20]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-NEGAMYCIN [J].
TANNER, D ;
SOMFAI, P .
TETRAHEDRON LETTERS, 1988, 29 (19) :2373-2376