Preparation of Disubstituted Phenyl Propargyl Alcohols, their Use in Oxathiolene Oxide Synthesis, and Evaluation of the Oxathiolene Oxide Products as Anticarcinogenic Enzyme Inducers

Author(s): Maben Ying, Matthew G. Smentek, Rong Ma, Cynthia S. Day, Suzy V. Torti, Mark E. Welker

Journal Name: Letters in Organic Chemistry

Volume 6 , Issue 3 , 2009

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A number of alkynols have been prepared by Sonogoshira coupling of propargyl alcohol to disubstituted aromatic halides. Chelation controlled addition of organometallic nucleophiles to these alkynols was then affected followed by the addition of sulfur dioxide. This methodology was used to prepare a number of oxathiolene oxides which have been screened as NQO1 (quinone oxidoreductase) inducers.

Keywords: Alkynol synthesis, cancer chemoprevention, sulfur heterocycle synthesis, NQO1

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Article Details

Year: 2009
Page: [242 - 251]
Pages: 10
DOI: 10.2174/157017809787893064

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