5-( Methylthio) tetrazoles as versatile synthons in the stereoselective synthesis of polycyclic pyrazolines via photoinduced intramolecular nitrile imine-alkene 1,3-dipolar cycloaddition

被引：22

作者：

Pla, Daniel ^{[1
]}

Tan, Derek S. ^{[1
,2
]}

Gin, David Y. ^{[1
,2
]}

机构：

[1] Mem Sloan Kettering Canc Ctr, Mol Pharmacol & Chem Program, New York, NY 10065 USA

[2] Mem Sloan Kettering Canc Ctr, Triinst Res Program, New York, NY 10065 USA

来源：

CHEMICAL SCIENCE | 2014年 / 5卷 / 06期

基金：

欧盟第七框架计划;

关键词：

NEWBOULDIA-LAEVIS; 1.3-DIPOLARE CYCLOADDITIONEN; RADICAL CYCLIZATION; COUPLING REACTION; BOND FORMATION; L-PROLINE; WITHASOMNINE; CHEMISTRY; NITRILIMINES; PROTEINS;

D O I：

10.1039/c4sc00107a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A key thioether substituent in readily accessible 2-alkyl-5-(methylthio)tetrazoles enables facile photoinduced denitrogenation and intramolecular nitrile imine 1,3-dipolar cycloaddition to afford a wide range of polycyclic pyrazoline products with excellent diastereoselectivity. The methylthio group red-shifts the UV absorbance of the tetrazole, obviating the requirement in all previous substrate systems for at least one aryl substituent, and can subsequently be converted into a variety of other functionalities. This synthetic platform has been applied to the concise total syntheses of the alkaloid natural products ( +/-)-newbouldine and withasomnine.

引用

页码：2407 / 2415

页数：9

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