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Report | Regular issue | Vol 14, No. 7, 1980, pp.975-984
Published online, 1st January, 1970
DOI: 10.3987/R-1980-07-0975
Selenium Dioxide Oxidations in the β-Carboline Area

Olivia Campos, Mike DiPierro Michael Cain, Robert Mantei, Ali Gawish, and James M. Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.

Abstract

The reaction of 1-ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 11 with selenium dioxide has resulted in the synthesis of the β-carboline alkaloids, 1-acetyl-3-methoxycarbonyl-β-carboline 14 and 1-acetyl-β-carboline 15. Application of this technology in a different series has resulted in a two step synthesis of canthin-6-one. The scope and/or limitations of the reaction of tetrahydro-β-carbolines with selenium dioxide are discussed.