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- W2951620121 abstract "Treatment of dihydrocodeinone (1a) or the 8 beta-methyl (1b) or 8 beta-ethyl (1c) analogues with formaldehyde-Ca(OH)2 in aqueous dioxane gave the corresponding 7,7-bis(hydroxymethyl)-6 beta-ols 2a-c. Ditosylation of 2, followed by LiEt3BH reduction, gave either the 7,7-dimethyl-6 beta-ol (6a) or 7 alpha-methyl-6 beta, 7 beta-oxetane compounds (5b,c). Compounds 5b and 5c were cleaved to 6b or 6c using LiAlH4-AlCl3. The configuration of the C6-alcohol group of 6a was confirmed by an oxidation-reduction sequence which gave the 7,7-dimethyl-5 alpha-ol 8a. Oxidation of 6 gave the C6-ketones 7a-c, which were converted to N-(cycloalkylmethyl) derivatives 11 and 12 and their corresponding 3-hydroxy compounds 14 and 15. The 3-methoxy-7,7-dimethyl-6-ones 7 were as active as dihydrocodeinone in agonist assays. One compound of this series, N-(cyclopropylmethyl)-7,7-dimethyldihydronorcodeinone (11a), was a potent mixed agonist-narcotic antagonist." @default.
- W2951620121 created "2019-06-27" @default.
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- W2951620121 creator A5004437103 @default.
- W2951620121 date "1981-11-03" @default.
- W2951620121 modified "2023-09-24" @default.
- W2951620121 title "ChemInform Abstract: ANALGESIC NARCOTIC ANTAGONISTS. 5. 7,7-DIMETHYLDIHYDROCODEINONES AND 7,7-DIMETHYLDIHYDROMORPHINONES" @default.
- W2951620121 cites W2028983284 @default.
- W2951620121 doi "https://doi.org/10.1002/chin.198144305" @default.
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