Synthesis of the C1-C12 fragment of fostriecin

被引:58
作者
Cossy, J [1 ]
Pradaux, F [1 ]
BouzBouz, S [1 ]
机构
[1] ESPCI, CNRS, Chim Organ Lab, F-75231 Paris 05, France
关键词
D O I
10.1021/ol016116x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The synthesis of the C-1-C-12 fragment of fostriecin was achieved from (S)-glycidol in 15 steps by using an enantioselective allytitanation reaction and a ring closure metathesis as the key steps.
引用
收藏
页码:2233 / 2235
页数:3
相关论文
共 17 条
[1]   Determination of the relative and absolute stereochemistry of fostriecin (CI-920) [J].
Boger, DL ;
Hikota, M ;
Lewis, BM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1748-1753
[2]   Total synthesis of fostriecin (CI-920) [J].
Boger, DL ;
Ichikawa, S ;
Zhong, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4161-4167
[3]   INHIBITION OF TYPE-II TOPOISOMERASE BY FOSTRIECIN [J].
BORITZKI, TJ ;
WOLFARD, TS ;
BESSERER, JA ;
JACKSON, RC ;
FRY, DW .
BIOCHEMICAL PHARMACOLOGY, 1988, 37 (21) :4063-4068
[4]   STUDIES ON THE BIOCHEMICAL-MECHANISM OF THE NOVEL ANTITUMOR AGENT, CI-920 [J].
FRY, DW ;
BORITZKI, TJ ;
JACKSON, RC .
CANCER CHEMOTHERAPY AND PHARMACOLOGY, 1984, 13 (03) :171-175
[5]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450
[6]   ENANTIOSELECTIVE ALLYLTITANATION OF ALDEHYDES WITH CYCLOPENTADIENYLDIALKOXYALLYLTITANIUM COMPLEXES [J].
HAFNER, A ;
DUTHALER, RO ;
MARTI, R ;
RIHS, G ;
ROTHESTREIT, P ;
SCHWARZENBACH, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2321-2336
[7]   The antitumor drug fostriecin induces vimentin hyperphosphorylation and intermediate filament reorganization [J].
Ho, DT ;
Roberge, M .
CARCINOGENESIS, 1996, 17 (05) :967-972
[8]   NOVEL ANTITUMOR AGENTS CI-920, PD 113270, AND PD 113271 .3. STRUCTURE DETERMINATION [J].
HOKANSON, GC ;
FRENCH, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (04) :462-466
[9]   THE PROTEIN PHOSPHATASES INVOLVED IN CELLULAR-REGULATION .1. CLASSIFICATION AND SUBSTRATE SPECIFICITIES [J].
INGEBRITSEN, TS ;
COHEN, P .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1983, 132 (02) :255-261
[10]   SYNTHESIS OF THE 5R, 8R, 9S, 11R DEPHOSPHORYLATED DERIVATIVE OF CI-920, A NOVEL ANTITUMOR AGENT [J].
JUST, G ;
OCONNOR, B .
TETRAHEDRON LETTERS, 1988, 29 (07) :753-756