An asymmetric total synthesis of (+)-(3R,4S,5R,7S)-neoclansenamide

被引:16
作者
Wang, JQ [1 ]
Tian, WS [1 ]
机构
[1] ACAD SINICA,SHANGHAI INST ORGAN CHEM,SHANGHAI 200032,PEOPLES R CHINA
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 02期
关键词
D O I
10.1039/p19960000209
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new hepatoprotective lactam (+)-(3R,4S,5R,7S)-neoclausenamide 1 isolated from the leaves of Chinese folk medicine Clausena lansium (Lour.) Skeel, has been readily synthesized from methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate in 22.0% overall yield.
引用
收藏
页码:209 / 212
页数:4
相关论文
共 10 条
[1]  
CHENG JC, 1989, CHINESE SCI BULL, V34, P957
[2]  
COOTE SJ, 1989, J CHEM SOC P1, P2222
[3]   OXIDATIVE HYDROLYSIS OF 1,3-DITHIANE DERIVATIVES TO CARBONYL COMPOUNDS USING N-HALOSUCCINIMIDE REAGENTS [J].
COREY, EJ ;
ERICKSON, BW .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3553-&
[4]   DIASTEREOSELECTIVE AND ENANTIOSELECTIVE TOTAL SYNTHESIS OF THE HEPATOPROTECTIVE AGENT CLAUSENAMIDE [J].
HARTWIG, W ;
BORN, L .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4352-4358
[5]  
HUANG DF, 1990, TETRAHEDRON, V46, P3135
[6]   A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES [J].
KOLB, HC ;
SHARPLESS, KB .
TETRAHEDRON, 1992, 48 (48) :10515-10530
[7]  
KWONG HL, 1990, TETRAHEDRON LETT, V31, P2999
[8]   LARGE-SCALE AND HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL C-13 SIDE-CHAIN THROUGH ASYMMETRIC DIHYDROXYLATION [J].
WANG, ZM ;
KOLB, HC ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :5104-5105
[9]  
YANG M-H, 1987, Yaoxue Xuebao, V22, P33
[10]  
YANG MH, 1987, ACTA CHIM SINICA, V3, P267