A Baylis-Hillman/ozonolysis route towards (±) 4,5-dihydroxy-2,3-pentanedione (DPD) and analogues

被引：28

作者：

Frezza, M ^{[1
]}

Soulère, L ^{[1
]}

Queneau, Y ^{[1
]}

Doutheau, A ^{[1
]}

机构：

[1] Inst Natl Sci Appl, UMR CNRS UCBL 5181, Chim Organ Lab, F-69621 Villeurbanne, France

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 38期

关键词：

quorum sensing; AI-2; Baylis-Hillman reaction; ozonolysis;

D O I：

10.1016/j.tetlet.2005.07.102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Baylis-Hillman reaction between 2-(tert-butyldimethylsilyloxy)ethanal and 3-buten-2-one followed by desilylation gave rise to the corresponding (alpha-methylene-beta,gamma-dihydroxy ketone further converted by reductive ozonolysis of the carbon-carbon double bond into racemic 4,5-dihydroxy-2,3-pentanedione (DPD), a significant molecule in bacterial cell-cell communication systems. The same sequence applied to other substrates allowed the preparation of chain elongated analogues and 5-O-acylated derivatives of DPD. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6495 / 6498

页数：4

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