PREPARATION OF A SEMISYNTHETIC ANALOG OF MEVINOLIN AND COMPACTIN

被引:22
作者
CLIVE, DLJ
WICKENS, PL
DASILVA, GVJ
机构
[1] Department of Chemistry, University of Alberta, Edmonton
关键词
D O I
10.1021/jo00122a037
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Enone 5, derived by chemical degradation of compactin (1), was elaborated into the semisynthetic analogue 4, which is an inhibitor of cholesterol biosynthesis in rat liver microsomes.
引用
收藏
页码:5532 / 5536
页数:5
相关论文
共 31 条
[1]
REACTIVITY OF 3,6-DIMETHOXY-3,6-DIMETHYLCYCLOHEXA-1,4-DIENE .3. REGIOSELECTIVE ALPHA-ARYLATION OF KETONES VIA THEIR SILYL ENOL ETHERS [J].
ALONSO, F ;
YUS, M .
TETRAHEDRON, 1991, 47 (43) :9119-9124
[2]
SYNTHESIS OF SYNVINOLIN - EXTREMELY HIGH CONVERSION ALKYLATION OF AN ESTER ENOLATE [J].
ASKIN, D ;
VERHOEVEN, TR ;
LIU, TMH ;
SHINKAI, I .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4929-4932
[3]
PENTAVALENT ORGANOBISMUTH REAGENTS .3. PHENYLATION OF ENOLS AND OF ENOLATE AND OTHER ANIONS [J].
BARTON, DHR ;
BLAZEJEWSKI, JC ;
CHARPIOT, B ;
FINET, JP ;
MOTHERWELL, WB ;
PAPOULA, MTB ;
STANFORTH, SP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2667-2675
[4]
TOWARDS A NEW TYPE OF HMG-COA REDUCTASE INHIBITORS .2. DRAMATIC SUBSTITUENTS EFFECTS IN THE C-5 EPIMERIZATION OF CARBOHYDRATE-DERIVATIVES [J].
BOQUEL, P ;
TAILLEFUMIER, C ;
CHAPLEUR, Y ;
RENAUT, P ;
SAMRETH, S ;
BELLAMY, FD .
TETRAHEDRON, 1993, 49 (01) :83-96
[5]
DIRECT AND REGIOCONTROLLED SYNTHESIS OF ALPHA-PHENYL KETONES FROM SILYL ENOL ETHERS AND DIPHENYLIODONIUM FLUORIDE [J].
CHEN, KC ;
KOSER, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5764-5767
[6]
CHEMICAL SYNTHESIS OF 3-ETHYLCOMPACTIN, AN INHIBITOR OF 3-HYDROXY-3-METHYLGLUTARYLCOENZYME-A REDUCTASE [J].
CLIVE, DLJ ;
MURTHY, KSK ;
GEORGE, R ;
POZNANSKY, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (07) :2099-2108
[7]
STUDIES ON THE DEGRADATION OF MEVINOLIN AND COMPACTIN - A FORMAL ROUTE TO SEMISYNTHETIC ANALOGS [J].
CLIVE, DLJ ;
ZHANG, CZ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1413-1427
[8]
TOTAL SYNTHESIS OF BOTH (+)-COMPACTIN AND (+)-MEVINOLIN - A GENERAL STRATEGY BASED ON THE USE OF A SPECIAL TITANIUM REAGENT FOR DICARBONYL COUPLING [J].
CLIVE, DLJ ;
MURTHY, KSK ;
WEE, AGH ;
PRASAD, JS ;
DASILVA, GVJ ;
MAJEWSKI, M ;
ANDERSON, PC ;
EVANS, CF ;
HAUGEN, RD ;
HEERZE, LD ;
BARRIE, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3018-3028
[9]
NOVEL SYNTHESIS OF MEVINOLIN-RELATED COMPOUNDS - LARGE-SCALE PREPARATION OF HMG-COA REDUCTASE INHIBITOR L-679,336 [J].
DECAMP, AE ;
MILLS, SG ;
KAWAGUCHI, AT ;
DESMOND, R ;
REAMER, RA ;
DIMICHELE, L ;
VOLANTE, RP .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3564-3571
[10]
ALPHA-ARYLATION VS ALPHA-ARYLHYDRAZONYLATION OF ALKYL ARYL KETONES WITH ARYLAZO TERT-BUTYL SULFIDES [J].
DELLERBA, C ;
NOVI, M ;
PETRILLO, G ;
TAVANI, C .
TETRAHEDRON, 1993, 49 (01) :235-242