从石松中首次分离得到的两种石松胺型生物碱——石松胺-V和-W的不对称全合成。

Asymmetric total syntheses of two phlegmarine-type alkaloids, lycoposerramines-V and -W, newly isolated from Lycopodium serratum.

作者信息

Shigeyama Takahide, Katakawa Kazuaki, Kogure Noriyuki, Kitajima Mariko, Takayama Hiromitsu

机构信息

Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

出版信息

Org Lett. 2007 Sep 27;9(20):4069-72. doi: 10.1021/ol701871v. Epub 2007 Sep 8.

DOI:10.1021/ol701871v

PMID:17824711

Abstract

Two new Phlegmarine-type alkaloids, lycoposerramines-V and -W, were isolated from Lycopodium serratum, and their structures including the absolute configuration were established by asymmetric total synthesis involving such key steps as Johnson-Claisen rearrangement, asymmetric allylation, and ring-closing metathesis (RCM)- or SmI(2)-mediated stereoselective piperidine ring construction.

摘要

从石松中分离出两种新的石松属型生物碱，石松胺-V和-W，并通过不对称全合成确定了它们的结构，包括绝对构型，该合成涉及Johnson-Claisen重排、不对称烯丙基化以及关环复分解（RCM）或SmI(2)介导的立体选择性哌啶环构建等关键步骤。