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
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MSK Authors
  1. Derek S Tan
    68 Tan
  2. David Y Gin
    41 Gin