Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of …

…, EC Pietsch, DR Pennella, SV Torti, ME Welker

Index: Franks, Marion A.; Schrader, Edward A.; Pietsch, E. Christine; Pennella, Daniel R.; Torti, Suzy V.; Welker, Mark E. Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 6 p. 2221 - 2233

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Citation Number: 15

Abstract

A number of alkynols have been prepared by Sonogashira coupling of propargyl alcohol to aromatic halides. Chelation-controlled addition of organometallic nucleophiles to these alkynols was then effected followed by the addition of the sulfur electrophiles, sulfur dioxide or thionyl chloride. This methodology was used to prepare a number of oxathiolene oxides, which have been screened as NQO1 (quinone oxidoreductase) inducers.