Synthesis of a novel 4,6′-epoxymorphinan derivative and a highly strained novel conjugated ketone

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• 作者：Toru Nemoto ; Hideaki Fujii ; Noriko Sato ; Hiroshi Nagase
• 关键词：Opioid ; Naltrexone ; 4 ; 6′ ; -Epoxymorphinan ; Analgesics
• 刊名：Tetrahedron Letters
• 出版年：2007
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：8 October 2007
• 卷：48
• 期：41
• 页码：7413-7417
• 文件大小：162 K

摘要

A modification of the 4,5-epoxymorphinan skeleton of naltrexone was carried out to improve the potency and the selectivity of the ligand for an opioid receptor subtype. As one of the modified structures, we newly designed and synthesized a novel 7-membered ring ether derivative, which had an inserted OCH₂ group between the 4- and 6-positions of the morphinan skeleton. The derivative with a 7-membered ring ether, 4,6′-epoxymorphinan, has a more fixed chair form than the 4,5-epoxymorphinan. In addition, we found a new cleavage reaction of the 4,5-epoxy ring in naltrexone, and also obtained a highly strained novel conjugated ketone.