番茄聚塞胺-V和5-表番茄聚塞胺-V的全合成。

Total syntheses of lycoposerramine-V and 5-epi-lycoposerramine-V.

作者信息

Zhang Lan-De, Zhou Ting-Ting, Qi Sen-Xing, Xi Jie, Yang Xiao-Liang, Yao Zhu-Jun

机构信息

State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing National Laboratory of Microstructures, Nanjing University, 22 Hankou Road, Nanjing 210093 (P. R. China).

出版信息

Chem Asian J. 2014 Oct;9(10):2740-4. doi: 10.1002/asia.201402614. Epub 2014 Aug 13.

DOI:10.1002/asia.201402614

PMID:25123493

Abstract

Enantioselective total syntheses of lycopodium alkaloids lycoposerramine-V and 5-epi-lycoposerramine-V have been accomplished. Features of the newly established total synthesis include: 1) introduction of the first chiral center with a scalable desymmetrization reaction of an meso-anhydride; 2) chemoselective functionalization of a bis-Weinreb-amide with Grignard addition; and 3) construction of the multifunctionalized cyclohexanone with a stereoselective intramolecular Michael addition.

摘要

石松生物碱lycoposerramine-V和5-表-lycoposerramine-V的对映选择性全合成已经完成。新建立的全合成的特点包括：1）通过内消旋酸酐的可扩展去对称化反应引入第一个手性中心；2）用格氏加成法对双 Weinreb 酰胺进行化学选择性官能团化；3）通过立体选择性分子内迈克尔加成构建多官能化环己酮。