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:	http://www.scopus.com/inward/record.url?eid=2-s2.0-84900321456&partnerID=40&md5=861594785c35a9efc4954bf566c54296
Notes:	Chem. Sci. -- Export Date: 2 June 2014 -- CODEN: CSHCC -- Source: Scopus

https://synapse.mskcc.org/synapse/works/has_related_data_chk/51846