5-BROMO-2-PYRONE - AN EASILY PREPARED AMBIPHILIC DIENE AND A SYNTHETIC EQUIVALENT OF 2-PYRONE IN MILD, THERMAL, DIELS-ALDER CYCLOADDITIONS

被引：59

作者：

AFARINKIA, K ^{[1
]}

POSNER, GH ^{[1
]}

机构：

[1] JOHNS HOPKINS UNIV,SCH ARTS & SCI,DEPT CHEM,BALTIMORE,MD 21218

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(00)74757-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Bromo-2-pyrone, a solid prepared easily in one-flask according to a new route (eq. 1), has been found to undergo smooth and highly regiocontrolled 2+4-cycloadditions between 25-100-degrees-C with both electron-poor and electron-rich dienophiles; subsequent radical debrominations produced halogen-free bicyclic lactones, including a precursor to a vitamin D steroid, thus showing 5-bromo-2-pyrone to be a practical and effective synthetic equivalent of 2-pyrone in thermal Diels-Alder cycloaddition.

引用

页码：7839 / 7842

页数：4

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