Unexpected Rearrangement Reactions of the 14-Aminonaltrexone Skeleton.

Kenta Maeda, Sayaka Ohrui, Akihisa Tokuda, Yasuyuki Nagumo, Naoshi Yamamoto, Ryuji Tanimura, Tsuyoshi Saitoh, Noriki Kutsumura, Hiroshi Nagase

Organic letters 2023 May 19

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The reaction of 14-aminonaltrexone with acetic anhydride was found to produce a range of different novel compounds between the free compound and its hydrochloride. The hydrochloride produced a compound with an acetylacetone moiety, whereas the free form produced a compound with a pyranopyridine moiety. Efforts to isolate reaction intermediates and density functional theory calculations have elucidated those formation mechanisms with both bearing the novel morphinan-type skeleton. Furthermore, a derivative with the acetylacetone moiety showed binding to opioid receptors.

Citation

Kenta Maeda, Sayaka Ohrui, Akihisa Tokuda, Yasuyuki Nagumo, Naoshi Yamamoto, Ryuji Tanimura, Tsuyoshi Saitoh, Noriki Kutsumura, Hiroshi Nagase. Unexpected Rearrangement Reactions of the 14-Aminonaltrexone Skeleton. Organic letters. 2023 May 19;25(19):3407-3411