A practical and efficient synthesis of (±)-camptothecin

被引:25
作者
Chavan, SP [1 ]
Venkatraman, MS [1 ]
机构
[1] Natl Chem Lab, Div Organ Chem Technol, Poona 411008, Maharashtra, India
关键词
glycine; Wittig reaction; intramolecular Michael reaction; DIBAL-H reduction; camptothecin;
D O I
10.1016/S0040-4039(98)01415-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient synthesis of (+/-)-camptothecin from glycine via an intramolecular Michael addition is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6745 / 6748
页数:4
相关论文
共 20 条
[1]   Total synthesis of (+)-camptothecin [J].
Ciufolini, MA ;
Roschangar, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1692-1694
[2]   A 10-STEP, ASYMMETRIC-SYNTHESIS OF (S)-CAMPTOTHECIN [J].
COMINS, DL ;
BAEVSKY, MF ;
HONG, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10971-10972
[3]   NEW 4+1 RADICAL ANNULATIONS - A FORMAL TOTAL SYNTHESIS OF (+/-)-CAMPTOTHECIN [J].
CURRAN, DP ;
LIU, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5863-5864
[4]   ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION-METAL COMPLEXES .5. PALLADIUM-CATALYZED ASYMMETRIC ALLYLATION OF ACTIVE METHINE COMPOUNDS [J].
HAYASHI, T ;
KANEHIRA, K ;
HAGIHARA, T ;
KUMADA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :113-120
[5]   CAMPTOTHECIN - CHEMISTRY, BIOGENESIS AND MEDICINAL CHEMISTRY [J].
HUTCHINSON, CR .
TETRAHEDRON, 1981, 37 (06) :1047-1065
[6]  
JEW SS, 1995, TETRAHEDRON-ASYMMETR, V6, P1248
[7]   REACTION OF SCHIFF-BASES ANIONS WITH 4-HALO-2-BUTENOATES - SELECTIVE SYNTHESIS OF ALPHA-CYCLOPROPYL AND GAMMA-UNSATURATED, DELTA-UNSATURATED ALPHA-AMINO-ACID DERIVATIVES [J].
JOUCLA, M ;
ELGOUMZILI, M ;
FOUCHET, B .
TETRAHEDRON LETTERS, 1986, 27 (15) :1677-1680
[8]   STUDIES ON THE SYNTHESES OF HETEROCYCLIC-COMPOUNDS .878. SYNTHESIS OF (+/-)-CAMPTOTHECIN AND (+/-)-10-METHOXYCAMPTOTHECIN VIA ENAMINE ANNULATION [J].
KAMETANI, T ;
OHSAWA, T ;
IHARA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (05) :1563-1568
[9]   SYNTHESIS OF WATER-SOLUBLE (AMINOALKYL)CAMPTOTHECIN ANALOGS - INHIBITION OF TOPOISOMERASE-I AND ANTITUMOR-ACTIVITY [J].
KINGSBURY, WD ;
BOEHM, JC ;
JAKAS, DR ;
HOLDEN, KG ;
HECHT, SM ;
GALLAGHER, G ;
CARANFA, MJ ;
MCCABE, FL ;
FAUCETTE, LF ;
JOHNSON, RK ;
HERTZBERG, RP .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :98-107
[10]  
KRAISS G, 1973, TETRAHEDRON LETT, P2359