TOTAL SYNTHESIS OF (+)-DIHYDROCOMPACTIN

被引：15

作者：

HAGIWARA, H

KONNO, M

UDA, H

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 12期

关键词：

D O I：

10.1039/c39920000866

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of (+)-dihydrocompactin 1 has been achieved by employing the double Michael reaction of 3-tert-butyldimethylsilyloxy-1-acetylcyclohexene with methyl crotonate as a key step.

引用

页码：866 / 868

页数：3

共 23 条

[1] DIHYDROMEVINOLIN, A POTENT HYPOCHOLESTEROLEMIC METABOLITE PRODUCED BY ASPERGILLUS-TERREUS [J].

ALBERSSCHONBERG, G ;

JOSHUA, H ;

LOPEZ, MB ;

HENSENS, OD ;

SPRINGER, JP ;

CHEN, J ;

OSTROVE, S ;

HOFFMAN, CH ;

ALBERTS, AW ;

PATCHETT, AA .

JOURNAL OF ANTIBIOTICS, 1981, 34 (05) :507-512

[2] 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

[3] 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

[4] SYNTHESIS OF (+)-DIHYDROCOMPACTIN AND (+)-COMPACTIN VIA VINYLSILANE TERMINATED CATIONIC CYCLIZATION [J].

BURKE, SD ;

DEATON, DN .

TETRAHEDRON LETTERS, 1991, 32 (36) :4651-4654

[5] 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

[6] 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

[7] TOTAL SYNTHESES OF ML-236A AND COMPACTIN BY COMBINING THE LACTONIC (SILYL) ENOLATE REARRANGEMENT AND ALDEHYDE-DIENE CYCLOCONDENSATION TECHNOLOGIES [J].

DANISHEFSKY, SJ ;

SIMONEAU, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2599-2604

[8] 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

[9] 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

[10] HIGH DIASTEREOSELECTION IN THE ALDOL REACTION OF THE BISTRIMETHYLSILYL ENOL ETHER OF METHYL ACETOACETATE WITH 2-BENZYLOXYHEXANAL - SYNTHESIS OF (-)-PESTALOTIN [J].

HAGIWARA, H ;

KIMURA, K ;

UDA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (06) :693-700

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