Using the Pummerer cyclization-deprotonation-cycloaddition cascade of imidosulfoxides for alkaloid synthesis

A Padwa, TM Heidelbaugh…

Index: Padwa, Albert; Heidelbaugh, Todd M.; Kuethe, Jeffrey T. Journal of Organic Chemistry, 2000 , vol. 65, # 8 p. 2368 - 2378

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Citation Number: 108

Abstract

The Pummerer reaction of imidosulfoxides bearing tethered alkenyl groups has been employed for the synthesis of several alkaloids. The required imidosulfoxides necessary for the cascade sequence were easily obtained by heating the appropriate amide with (ethylsulfenyl) acetyl chloride followed by sodium periodate oxidation. The initially formed thionium ion, obtained by treating the imidosulfoxide with acetic anhydride and p- ...

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