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

ABSTRACT: Methodology is presented for the synthesis of 6α/β-3-dehydroxynaltrexamines and 6α/β-N-methyl-3-dehydroxynaltrexamines. A stereoselective route is provided for each target compound while a novel one-pot method for the synthesis of 6 α/β-3-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.

SUBMITTER: Li M

PROVIDER: S-EPMC7584067 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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

Li Mengchu M St Onge Celsey M CM Zhang Yan Y

Tetrahedron letters 20200820 39

Methodology is presented for the synthesis of 6α/β-3-dehydroxynaltrexamines and 6α/β- N-methyl-3-dehydroxynaltrexamines. A stereoselective route is provided for each target compound while a novel one-pot method for the synthesis of 6 α/β-3-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 ...[more]

PMID: 33100417

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