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- W1978006448 abstract "Carbocyclic nucleosides are of considerable interest for the development of new therapeutic agents. A key reaction in the preparation of many such nucleoside analogues is dihydroxylation of appropriately substituted cyclopentenes. Although often considered a routine reaction, in this paper, we report the dramatic influence of substituents on the facial selectivity of dihydroxylations. The substituted cyclopentene substrates are derived from acylnitroso cycloaddition reactions of cyclopentadiene, followed by N−O reduction and efficient enzymatic resolution. The results are directly utilized in a very efficient asymmetric synthesis of an antiviral carbocyclic nucleoside, noraristeromycin 5. Extensions toward the synthesis of carbocyclic sinefungin 7 document the importance of realizing the substituent dependence of the dihydroxylation reaction." @default.
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- W1978006448 date "2006-05-01" @default.
- W1978006448 modified "2023-09-26" @default.
- W1978006448 title "Substrate-Dependent Dihydroxylation of Substituted Cyclopentenes: Toward the Syntheses of Carbocyclic Sinefungin and Noraristeromycin" @default.
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- W1978006448 doi "https://doi.org/10.1021/jo060224l" @default.
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