Studies towards the synthesis of secoiridoids

TETRAHEDRON

卷:71

Article

Wu, Shaoping^1,2,3  Zhang, Yongmin^1,2,3  Agarwal, Jyoti^1,2  Mathieu, Emilie^1,2  Thorimbert, Serge^1,2  Dechoux, Luc^1,2 

[1] Univ Paris 06, Sorbonne Univ, Inst Parisien Chim Mol, UMR 8232, F-75005 Paris, France

[2] CNRS, UMR8232, F-75005 Paris, France

[3] NW Univ Xian, Biomed Key Lab Shaanxi Prov, Xian 710069, Shaanxi, Peoples R China

关键词: Secoiridoids;    Gentiopicroside;    Organocatalysis;    [3+3] Cycloadditions;    N-heterocyclic-carbenes;   

DOI  :  10.1016/j.tet.2015.07.067

来源: Elsevier

【 摘 要 】

A new approach to secoiridoids, based on the synthesis of the key functionalized intermediates 4 and 5, is presented. These compounds were tested in formal [3+3] cycloadditions. Acyl-chloride 15 was transformed into enol alpha,beta-unsaturated ester 16, which was involved in a N-heterocyclic carbene rearrangement to give an advanced precursor 17 in the total synthesis of secoiridoids. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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