THE BICYCLO[2.1.0]PENTANE WAY TO THE DIQUINANE ALCOHOL PART OF NATURAL TRIQUINANES - A HIGH-YIELD ACCESS STARTING FROM TRIMETHYLSILYLOXYCYCLOPENTENE

被引：27

作者：

FRANCKNEUMANN, M

MIESCH, M

GROSS, L

机构：

[1] Laboratoire de Chimie Organique Synthétique, associé au CNRS, Institut de Chimie, 67008 STRASBOURG, 1, rue Blaise Pascal

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(00)97796-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trimethylsilyloxycyclopentene reacts exclusively with ethyl propiolate in the presence of ZrCl4 to give a [2+2] adduct (alcohol 6, 90 %). After protection, the stereoselective cyclopropanation via 1,3-dipolar addition of 2-diazopropane followed by sensitized photocleavage, leads with good yields to the bicyclo [2.1.0] pentane derivative 11. By deprotection and solvolytic cleavage with dilute mineral acid, the diquinane alcohol 5 is obtained quantitatively and stereospecifically. © 1990.

引用

页码：5027 / 5030

页数：4

共 12 条

[1]

BRANNOCK KC, 1968, J ORG CHEM, V29, P818

[2] [2+2] CYCLOADDITION OF ETHYL PROPIOLATE AND SILYL ENOL ETHERS [J].

CLARK, RD ;

UNTCH, KG .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (02) :248-253

[3]

FRANCKNEUMANN M, 1968, TETRAHEDRON LETT, P2979

[4] TOTAL CYCLOPROPENE SYNTHESIS OF A NATURAL ANGULAR TRIQUINANE, (+/-)-SILPHINENE [J].

FRANCKNEUMANN, M ;

MIESCH, M ;

LACROIX, E .

TETRAHEDRON LETTERS, 1989, 30 (27) :3533-3536

[5]

FRANCKNEUMANN M, 1989, SYNTHESIS-STUTTGART, P820

[6] CYCLOPROPENE SYNTHESIS OF ILLUDINE-M DERIVATIVES [J].

FRANCKNEUMANN, M ;

MIESCH, M ;

BARTH, F .

TETRAHEDRON LETTERS, 1989, 30 (27) :3537-3540

[7] TOTAL CYCLOPROPENE SYNTHESIS OF A NATURAL LINEAR TRIQUINANE, (+/-)-HIRSUTENE [J].

FRANCKNEUMANN, M ;

MIESCH, M ;

LACROIX, E .

TETRAHEDRON LETTERS, 1989, 30 (27) :3529-3532

[8]

FRANCKNEUMANN M, 1968, ANGEW CHEM, V80, P42

[9]

FRANCKNEUMANN M, IN PRESS TETRAHEDRON

[10]

FRANCKNEUMANN M, 1969, ANGEW CHEM, V81, P189

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