A convenient route to 2,6-dialkyl-2,3-dihydro-4H-pyran-4-ones via oxidative cleavage of protected 1-(2-oxoalkyl)-cyclopropanols. Synthesis of (±)-hepialone and its natural congener

被引：12
|
作者：
Astashko, Dmitry A. [1 ]
Tyvorskii, Vladimir I. [1 ]
机构：
[1] Belarusian State Univ, Dept Organ Chem, Minsk 220030, BELARUS
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 37期
关键词：
Cyclopropanols; Oxidation; beta-Hydroxyketones; Pheromones; TITANIUM-MEDIATED CYCLOPROPANATION; ONE-POT SYNTHESIS; GRIGNARD-REAGENTS; CARBOXYLIC ESTERS; CYCLIZATION; IDENTIFICATION; DERIVATIVES; SELECTIVITY; PHEROMONES; MECHANISM;
D O I：
10.1016/j.tetlet.2011.07.042
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient strategy for the synthesis of 2,6-dialkyl-2,3-dihydro-4H-pyran-4-ones has been developed, the key steps of which are oxidative cleavage of the three-membered rings of 1-(2-oxoalkyl)-cyclopropanols and acid-promoted cyclization of the resulting beta-hydroxyketones. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4792 / 4794
页数：3
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