A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids

被引：12

作者：

Urbitsch, Felix ^{[1
]}

Elbert, Bryony L. ^{[1
]}

Llaveria, Josep ^{[2
]}

Streatfeild, Penelope E. ^{[1
]}

Anderson, Edward A. ^{[1
]}

机构：

[1] Chem Res Lab, Oxford OX1 3TA, England

[2] UCB Pharma Ltd, Slough SL1 3WE, Berks, England

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 04期

基金：

英国工程与自然科学研究理事会;

关键词：

CROSS-COUPLING REACTIONS; 1ST TOTAL-SYNTHESIS; MEDIUM-SIZED RINGS; STEREOSELECTIVE-SYNTHESIS; KINETIC RESOLUTION; GENERAL-SYNTHESIS; LIPID MEDIATORS; REDUCTION; INFLAMMATION; EPOXIDATION;

D O I：

10.1021/acs.orglett.0c00089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation. Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama-Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fragments, and control the stereochemistry of the natural product (Z)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive investigations of resolvin biology.

引用

页码：1510 / 1515

页数：6

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