Total Synthesis of 15-D2t- and 15-epi-15-E2t-Isoprostanes

被引：22

作者：

Brinkmann, Yasmin ^{[1
]}

Oger, Camille ^{[1
]}

Guy, Alexandre ^{[1
]}

Durand, Thierry ^{[1
]}

Galano, Jean-Marie ^{[1
]}

机构：

[1] Univ Montpellier 2, Fac Pharm, Univ Montpellier 1, Inst Biomol Max Mousseron,IBMM,CNRS,UMR 5247, F-34093 Paris 05, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 07期

关键词：

ENANTIOMERICALLY PURE DIASTEREOMERS; SECONDARY ALCOHOLS; IN-VIVO; ISOPROSTANES; BIOCHEMISTRY; PHARMACOLOGY; MEDIATORS; MANDELATE; PRODUCTS; BIOLOGY;

D O I：

10.1021/jo1000274

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of 15-D-2t-isoprostane is described. (-)-(9S, 15S)-15-D-2t-IsoP 1 and (+)-(11R, 15R)-15-epi-15-E-2t-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.

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收藏

页码：2411 / 2414

页数：4

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