EFFICIENT INTRAMOLECULAR C-H INSERTION BY AN ALKYLIDENE CARBENE GENERATED FROM A VINYL-CHLORIDE

被引：34

作者：

TABER, DF

SAHLI, A

YU, H

MEAGLEY, RP

机构：

[1] Department of Chemistry and Biochemistry, University of Delaware, Newark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 20期

关键词：

D O I：

10.1021/jo00125a050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It is observed that chloride 4 on exposure to sodium bis(trimethylsilyl)amide smoothly generates the cyclopentene 5, by insertion of the intermediate alkylidene carbene into the methine C-H. Chloride 4 is prepared in several steps from L-tartaric acid. On ozonolysis and subsequent aldol condensation, 5 is transformed into 1, a synthon for the A ring of taxol 2.

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页码：6571 / 6573

页数：3

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