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

页码：4792 / 4794

页数：3

共 38 条

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