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- W2093291251 abstract "The palladium-catalyzed substitution of acylated (1R,5R,8R)- and (1R,5R,8S)-8-hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-ones has been studied using a number of C- and N-nucleophiles. In all cases, the exo derivatives (8R) were found to be more reactive than the corresponding endo derivatives (8S). The reaction was found to give good yields and a single product when sodium dimethyl malonate was used as the nucleophile. However, when less reactive C- and N-nucleophiles were employed, the reaction gave inseparable mixtures of both C-6 and C-8 substituted products, thus limiting the synthetic use of the reaction with these nucleophiles. Additionally, Mitsunobu substitution of (1R,5R,8R)-8-hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-one (3) with 6-chloropurine, followed by reduction of the lactone moiety and treatment with liquid ammonia, gave the carbocyclic nucleoside (1S,2R,3R)-9-[2-hydroxy-3-(2-hydroxyethyl)cyclopent-4-en-1-yl]-9H-adenine (19), which can be viewed as an analogue of the carbocyclic nucleoside BCA." @default.
- W2093291251 created "2016-06-24" @default.
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- W2093291251 date "2001-03-01" @default.
- W2093291251 modified "2023-09-23" @default.
- W2093291251 title "A Study on the Allylic Substitution of (1R,5R,8R)- and (1R,5R,8S)-8-Hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-one Derivatives − Preparation of (1S,2R,3R)-9-[2-Hydroxy-3-(2-hydroxyethyl)cyclopent-4-en-1-yl]-9H-adenine" @default.
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- W2093291251 doi "https://doi.org/10.1002/1099-0690(200103)2001:6<1129::aid-ejoc1129>3.0.co;2-t" @default.
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