Expedient synthesis of a highly substituted tropolone via a 3-oxidopyrylium [5+2] cycloaddition reaction

被引：28
|
作者：
Baldwin, JE
Mayweg, AVW
Pritchard, GJ
Adlington, RM
机构：
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 24期
关键词：
D O I：
10.1016/S0040-4039(03)00987-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An expedient ten-step synthesis Of a substituted tropolone is described. The synthesis involves a 3-oxidopyrylium [5+2] cycloaddition reaction with acrylonitrile as the key step, affording a highly functionalized [3.2.1]-bicycle 10 as a single regioisomer. The nitrile substituent of the reduced cycloadduct 12 permits efficient ether-bridge cleavage and tropolone 15 is obtained after a final bis-oxidation procedure. The pyranulose acetate cycloaddition precurser was derived from 3-methyl-2-furoate. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4543 / 4545
页数：3
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