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A Novel and Efficient Synthesis of 14-Alkoxy-Substituted Indolo- and Benzofuromorphinans in the Series of Selective δ Opioid Receptor Antagonists

✍ Scribed by Helmut Schmidhammer; Peter Schwarz; Zhong-Yong Wei


Publisher
John Wiley and Sons
Year
1998
Tongue
German
Weight
569 KB
Volume
81
Category
Article
ISSN
0018-019X

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✦ Synopsis


A novel and more efficient synthesis of 14-alkoxy-substituted indolo-and benzofuro-morphinans in three steps starting from either naltrindole (1) or naltriben (2). using methoxymethyl or silyl protecting groups, is reported. The 14-0-alkyl group is introduced at the penultimate step of the procedure. This is an additional advantage of the described procedure since the late introduction of the 14-0-alkyl group makes it much easier to produce a greater diversity of 14-alkoxy derivatives in this series of 6 opioid receptor antagonists. Thus, compounds 14-19, 20-25, and 27-29 were synthesized.


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