A RING CONTRACTION OF 6-ALKOXY-2,3-DIHYDRO-6H-PYRAN-3-ONES TO POLYFUNCTIONALIZED CYCLOPENTENONES

被引：20

作者：

KOLB, HC ^{[1
]}

HOFFMANN, HMR ^{[1
]}

机构：

[1] UNIV HANNOVER,DEPT ORGAN CHEM,SCHNEIDERBERG 1B,W-3000 HANNOVER,GERMANY

来源：

TETRAHEDRON | 1990年 / 46卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(01)87820-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rearrangement of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (1) to trans-4-alkoxy-5-hydroxy-2-cyclopenten-1-ones (2) has been optimized. The effect of buffer concentration (PhCO2 H/KOAc) on reaction rate and yield suggests specific acid catalysis. Substitution patterns and influence of the 6-alkoxy substituent have been investigated. Applications in natural product synthesis are described. © 1990.

引用

页码：5127 / 5144

页数：18

共 23 条

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