期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 71, 期 11, 页码 4164-4169出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo060224l
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资金
- NIGMS NIH HHS [R01 GM68012, R01 GM068012-04, R01 GM068012-01, R01 GM068012-03, R01 GM068012-02, R01 GM068012] Funding Source: Medline
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.
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