An Enantioselective Strategy for the Synthesis of (S)-Tylophorine via One-Pot Intramolecular Schmidt/Bischler-Napieralski/Imine-Reduction Cascade Sequence

被引：30

作者：

Su, Bo ^{[1
]}

Chen, Fazhong ^{[1
]}

Wang, Qingmin ^{[1
]}

机构：

[1] Nankai Univ, Res Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期

基金：

中国国家自然科学基金;

关键词：

SCHMIDT REACTION; ALKYL AZIDES; ASYMMETRIC-SYNTHESIS; CYTOTOXIC ACTIVITY; TYLOPHORINE; ALKALOIDS; GENERATION; REACTIVITY; PROLINE; CATION;

D O I：

10.1021/jo302725q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel enantioselective strategy for the total synthesis of (S)-tylophorine was developed in an overall yield of 48% with more than 99% ee from readily avaliable azido acid and phenanthryl alcohol. This route features an Evans stereoselective alkylation and an unprecedented one pot intramolecular Schmidt/Bischler-Napieralski/imine-reduction cascade sequence, in which three new bonds and two rings formed in 84% yield. The intramolecular Schmidt rearrangement of the azido aldehyde was proved to be racemization-free.

引用

页码：2775 / 2779

页数：5

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