Stereoselective synthesis of HIV-1 protease inhibitor, DMP 323

…, LA Radesca, L Storace, RE Waltermire…

Index: Pierce; Pierce, Michael E.; Harris; Harris, Gregory D.; Islam; Islam, Qamrul; Radesca; Radesca, Lilian A.; Storace; Storace, Louis; Waltermire; Waltermire, Robert E.; Wat; Wat, Ed; Jadhav; Jadhav, Prabhakar K.; Emmett; Emmett, George C. Journal of Organic Chemistry, 1996 , vol. 61, # 2 p. 444 - 450

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Citation Number: 57

Abstract

DMP 323, a potent HIV-1 protease inhibitor, has been synthesized by an efficient stereoselective process, amenable to large scale preparations. The core C 2 symmetric diol was synthesized by a stereoselective pinacol coupling of CBZ protected d-phenylalanine. Judicious selection of protecting groups allowed cyclic urea formation under mild conditions, enhanced the ease of bis-alkylation, and led to intermediates which were easily purified ...