Approaches to installing a N-gem-dimethylmethylene-2-oxazolyl group and application to the synthesis of a second generation HIV protease inhibitor

…, J Liu, DE Petrillo, JF Leone, J Laquidara, B Marcune…

Index: Ikemoto, Norihiro; Miller, Ross A.; Fleitz, Fred J.; Liu, Jinchu; Petrillo, Daniel E.; Leone, Joseph F.; Laquidara, Joseph; Marcune, Benjamin; Karady, Sandor; Armstrong III, Joseph D.; Volante, Ralph P. Tetrahedron Letters, 2005 , vol. 46, # 11 p. 1867 - 1871

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Citation Number: 12

Abstract

Two syntheses of the title compound were developed based on different approaches for installing the oxazole ring moiety. Formation and dehydration of ketoamide was initially used and scaled up to afford on several kilogram scale, then oxazolyl anion/iminium coupling reaction was developed for a more convergent approach.