AN EFFICIENT ROUTE TO THE FORMAL TOTAL SYNTHESIS OF A-SECO MEVINIC ACID ANALOGS

被引：5

作者：

ARSENIYADIS, S

BRONDIALVES, R

WANG, Q

YASHUNSKY, DV

POTIER, P

机构：

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(00)78393-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short, stereocontrolled access to the fully functionalized B-ring together with a chemobiological approach to the 1,2,3,4-tetrasubstituted cyclohexene unit of A-seco mevinic acids is presented.

引用

页码：7949 / 7952

页数：4

共 19 条

[1] MEVINOLIN - A HIGHLY POTENT COMPETITIVE INHIBITOR OF HYDROXYMETHYLGLUTARYL-COENZYME-A REDUCTASE AND A CHOLESTEROL-LOWERING AGENT [J].

ALBERTS, AW ;

CHEN, J ;

KURON, G ;

HUNT, V ;

HUFF, J ;

HOFFMAN, C ;

ROTHROCK, J ;

LOPEZ, M ;

JOSHUA, H ;

HARRIS, E ;

PATCHETT, A ;

MONAGHAN, R ;

CURRIE, S ;

STAPLEY, E ;

ALBERSSCHONBERG, G ;

HENSENS, O ;

HIRSHFIELD, J ;

HOOGSTEEN, K ;

LIESCH, J ;

SPRINGER, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (07) :3957-3961

[2] REDUCTION OF ACID-CHLORIDES WITH SODIUM-BOROHYDRIDE IN N,N-DIMETHYLFORMAMIDE - NATURE OF THE REACTION INTERMEDIATE AND A METHOD FOR ITS CONVERSION TO THE CORRESPONDING ALDEHYDE WITH MINIMAL ALCOHOL FORMATION [J].

BABLER, JH ;

INVERGO, BJ .

TETRAHEDRON LETTERS, 1981, 22 (01) :11-14

[3] AN IMPROVED PROCEDURE FOR THE INTRODUCTION OF THE DELTA-LACTONE PORTION OF HMG-COA REDUCTASE INHIBITORS [J].

BLACKWELL, CM ;

DAVIDSON, AH ;

LAUNCHBURY, SB ;

LEWIS, CN ;

MORRICE, EM ;

REEVE, MM ;

ROFFEY, JAR ;

TIPPING, AS ;

TODD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1935-1937

[4] CRYSTAL AND MOLECULAR-STRUCTURE OF COMPACTIN, A NEW ANTIFUNGAL METABOLITE FROM PENICILLIUM-BREVICOMPACTUM [J].

BROWN, AG ;

SMALE, TC ;

KING, TJ ;

HASENKAMP, R ;

THOMPSON, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (11) :1165-1173

[5] MONACOLIN-K, A NEW HYPOCHOLESTEROLEMIC AGENT PRODUCED BY A MONASCUS SPECIES [J].

ENDO, A .

JOURNAL OF ANTIBIOTICS, 1979, 32 (08) :852-854

[6] ML-236A, ML-236B, AND ML-236C, NEW INHIBITORS OF CHOLESTEROGENESIS PRODUCED BY PENICILLIUM CITRINUM [J].

ENDO, A ;

KURODA, M ;

TSUJITA, Y .

JOURNAL OF ANTIBIOTICS, 1976, 29 (12) :1346-1348

[7] STEREOSELECTIVE SYNTHESIS OF THE TETRASUBSTITUTED CYCLOHEXANE CORE OF A MONOCYCLIC MEVINIC ACID ANALOG [J].

ERMOLENKO, MS ;

OLESKER, A ;

LUKACS, G .

TETRAHEDRON LETTERS, 1994, 35 (05) :711-714

[8] HYPOCHOLESTEROLEMIC AGENT COMPACTIN (ML-236B) - TOTAL SYNTHESIS OF THE HEXAHYDRONAPHTHALENE PORTION [J].

FUNK, RL ;

ZELLER, WE .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) :180-182

[9] ENZYMATIC RESOLUTION OF RACEMIC BICYCLIC LACTONES BY HORSE LIVER ESTERASE [J].

GUIBEJAMPEL, E ;

ROUSSEAU, G ;

BLANCO, L .

TETRAHEDRON LETTERS, 1989, 30 (01) :67-68

[10] SYNTHESIS AND BIOLOGICAL EVALUATION OF A MONOCYCLIC, FULLY FUNCTIONAL ANALOG OF COMPACTIN [J].

HEATHCOCK, CH ;

DAVIS, BR ;

HADLEY, CR .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (01) :197-202

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