SYNTHESIS OF THE ANGULAR TRIQUINANE (+/-)-PENTALENENE VIA SMALL RING INTERMEDIATES

被引：26

作者：

FRANCKNEUMANN, M

MIESCH, M

GROSS, L

机构：

[1] Laboratoire de Chimie Organique Synthétique, associé au CNRS, Institut de Chimie, 67000 Strasbourg, 1, rue Blaise Pascal

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 27期

关键词：

CYCLOBUTENE HYDROXY ESTERS; BICYCLO [2.1.0] PENTAN-2-OLS; DIQUINANES; 2+2] CYCLOADDITION; DIAZOALKANES; 1,3-DIPOLAR ADDITION; SILYL ENOL ETHERS; SILYL-ASSISTED NAZAROV REACTION; PENTALENENE;

D O I：

10.1016/S0040-4039(00)74809-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dimethyl t-butylsilyl enol ethers of cycloalkanones react with ethyl propynoate in the presence of ZrCl4 to give protected cyclobutenic hydroxy esters. Cyclopropanation by cycloaddition of diazoalkanes followed by sensitized photocleavage, leads to bicyclo [2.1.0] pentan-2-ol derivatives which are then cleaved with acids to 3-cyclopenten-1-ols. This reaction sequence was used for the synthesis of the angular triquinane (+/-)-pentalenene, starting from 3,3-dimethylcyclopentanone and diazoethane (--> ring A and B), the ring C being obtained by a silyl-assisted Nazarov type cyclization.

引用

页码：3879 / 3882

页数：4

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