Tetrahedron letters

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

M Frezza, L Soulère, Y Queneau, A Doutheau

文献索引：Frezza, Marine; Soulere, Laurent; Queneau, Yves; Doutheau, Alain Tetrahedron Letters, 2005 , vol. 46, # 38 p. 6495 - 6498

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被引用次数: 28

摘要

The Baylis–Hillman reaction between 2-(tert-butyldimethylsilyloxy) ethanal and 3-buten-2- one followed by desilylation gave rise to the corresponding α-methylene-β, γ-dihydroxy ketone further converted by reductive ozonolysis of the carbon–carbon double bond into racemic 4, 5-dihydroxy-2, 3-pentanedione (), a significant molecule in bacterial cell–cell communication systems. The same sequence applied to other substrates allowed the ...