Studies toward the large-scale synthesis of the HIV proteinase inhibitor Ro 31-8959

…, DJ Bushnell, PH Crackett, SJ Dunsdon…

Index: Parkes, Kevin E. B.; Bushnell, David J.; Crackett, Peter H.; Dunsdon, Stephen J.; Freeman, Andrew C.; et al. Journal of Organic Chemistry, 1994 , vol. 59, # 13 p. 3656 - 3664

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Citation Number: 124

Abstract

Ro 31-8959 (11, a potent and selective inhibitor of HIV proteinase, is currently in phase I11 clinical trials. Six approaches for the large-scale synthesis of this compound have been studied. All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5. They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and ...