Synthesis of novel pyranoquinones using an acyl radical cyclization strategy

被引：16

作者：

Donner, Christopher D. ^{[1
,2
]}

Casana, Myriam I. ^{[3
]}

机构：

[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

[2] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia

[3] Univ Strasbourg, Sch Chem Polymers & Mat Sci, ECPM, F-67000 Strasbourg, France

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 09期

基金：

澳大利亚研究理事会;

关键词：

Acyl radical cyclization; Polarity reversal catalysis; Pyranonaphthoquinone; Frenolicin B; NATURAL-PRODUCT SYNTHESIS; ORGANIC-SYNTHESIS; INHIBITORS; ETHERS;

D O I：

10.1016/j.tetlet.2011.12.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The thiol-catalysed cyclization of acyl radicals generated directly from benzaldehyde precursors has been investigated. Hindered beta-benzyloxyacrylates cyclize efficiently providing a tin-free radical cyclization approach to the serine/threonine kinase AKT inhibitor frenolicin B, whilst gamma-aryloxy crotonates give good yields of benzopyran-4-ones. This method is applied to the synthesis of a novel tetracyclic analogue of the pyranonaphthoquinone antibiotics. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

引用

页码：1105 / 1107

页数：3

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