Total Synthesis of Wasabidienones B1 and B0 via SIBX-Mediated Hydroxylative Phenol Dearomatization

被引：60

作者：

Pouysegu, Laurent ^{[1
,2
]}

Marguerit, Melanie ^{[1
,2
]}

Gagnepain, Julien ^{[1
,2
]}

Lyvinec, Gildas ^{[1
,2
]}

Eatherton, Andrew J. ^{[3
]}

Quideau, Stephane ^{[1
,2
]}

机构：

[1] Univ Bordeaux, Inst Mol Sci, CNRS, UMR 5255, F-33607 Pessac, France

[2] Inst Europeen Chim & Biol, F-33607 Pessac, France

[3] GlaxoSmithKline, Harlow CM195AW, Essex, England

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 22期

关键词：

D O I：

10.1021/ol802183p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the natural nondimerizing o-quinol (+)-wasabidienone B-1 was achieved from commercially available 1,3,5-trimethoxybenzene. The key dearomatizing transformation was efficiently accomplished via a hydroxylative phenol dearomatization reaction using the stabilized lambda(5)-iodane reagent IBX (SIBX). (+)-Wasabidienone B-1 was then converted into its congener (-)-wasabidienone B-0 via an improved thermally induced ring-contracting isomerization reaction.

引用

页码：5211 / 5214

页数：4

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