A reiterative synthesis of trans-fused polypyrans via tungsten pentacarbonyl-promoted alkynol endocyclization

被引：46

作者：

Bowman, JL ^{[1
]}

McDonald, FE ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 11期

关键词：

D O I：

10.1021/jo980058k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Endocyclization of 1-alkyn-5-ols occurs in the presence of tungsten pentacarbonyl-THF complex to give cyclic six-membered tungsten oxacarbenes which are easily converted to alpha-stannyl enol ethers by treatment with Bu3SnOTf and Et3N. These stannylated dihydropyrans undergo organocuprate-mediated alkylation to provide 6-(2-propynyl)-3,4-dihydro-2H-pyrans. Oxidation of these propargylated dihydropyrans with m-CPBA followed by reduction with Et3SiH under Lewis acid conditions generates another trans-fused 1-alkyn-5-ol. Repetition of this process provides are iterative synthesis of trans-fused polypyrans.

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页码：3680 / 3682

页数：3

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