Synthesis of 5β-methyl-6-demethoxythebaine and its Diels-Alder reaction to 6α,14α-ethenoisomorphinans and 6β,14β-ethenomorphinans (Chemistry of Opium Alkaloids, Part XXXV
✍ Scribed by R. H. Woudenberg; D. P. Piet; A. Sinnema; T. S. Lie; L. Maat
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 995 KB
- Volume
- 110
- Category
- Article
- ISSN
- 0165-0513
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## Abstract Mesylation of 7‐acetoxyneopine (4), followed by reductive cleavage of the acetyl group gave 6α‐__O__‐mesyl‐7α‐hydroxyneopine (6), in which the hydroxyl group was protected as a methoxymethoxy group. Elimination of the mesyl ester yielded 7‐(methoxymethoxy)‐6‐demethoxythebaine (7). For t
## Abstract 5β‐Ethylthebaine (3), together with 5β‐butylthebaine (4), was obtained from thebaine (1) after reaction with butyllithium and ethyl iodide. With butyllithium and diethyl sulfate, thebaine yielded 5β‐ethylthebaine (3), 5β, 10α‐diethylthebaine (5), and 5β, 10α, 10β‐triethylthebaine (6). T