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Stereoselective syntheses of 3-dehydroxynaltrexamines and N-methyl-3-dehydroxynaltrexamines. 2020

Mengchu Li, and Celsey M St Onge, and Yan Zhang
Department of Medicinal Chemistry, Virginia Commonwealth University, 800 E Leigh St, Richmond, VA, 23298, USA.

Methodology is presented for the synthesis of 6-dehydroxynaltrexamines and 6 N-methyl-3-dehydroxynaltrexamines. A stereoselective route is provided for each target compound while a novel one-pot method for the synthesis of 6 -N-methyl-3-dehydroxynaltrexamines is also explored. These results enable the versatile and efficient preparation of key epoxymorphinan intermediates to facilitate future selective opioid ligand discovery and development.

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