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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