5-(Methylthio)tetrazoles as versatile synthons in the stereoselective synthesis of polycyclic pyrazolines via photoinduced intramolecular nitrile imine-alkene 1,3-dipolar cycloaddition Journal Article
| Authors: | Pla, D.; Tan, D. S.; Gin, D. Y. |
| Article Title: | 5-(Methylthio)tetrazoles as versatile synthons in the stereoselective synthesis of polycyclic pyrazolines via photoinduced intramolecular nitrile imine-alkene 1,3-dipolar cycloaddition |
| Abstract: | 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. This journal is © the Partner Organisations 2014. |
| Journal Title: | Chemical Science |
| Volume: | 5 |
| Issue: | 6 |
| ISSN: | 2041-6520 |
| Publisher: | Royal Society of Chemistry |
| Date Published: | 2014-01-01 |
| Start Page: | 2407 |
| End Page: | 2415 |
| Language: | English |
| DOI: | 10.1039/c4sc00107a |
| PROVIDER: | scopus |
| PMCID: | PMC4126266 |
| PUBMED: | 25114776 |
| DOI/URL: | |
| Notes: | Chem. Sci. -- Export Date: 2 June 2014 -- CODEN: CSHCC -- Source: Scopus |
