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. 2006 May 26;71(11):4164-9.
doi: 10.1021/jo060224l.

Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin

May Xiao-Wu Jiang  1 , Bohan Jin, Jennifer L Gage, Alain Priour, Gordon Savela, Marvin J Miller
Affiliations

Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin

May Xiao-Wu Jiang et al. J Org Chem. .

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.

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References

    1. For a discussion of inhibitors of enzymes involved with purine and pyrimidine metabolism, see: Hobbs JB. In: Comprehensive Medicinal Chemistry. Hansch C, editor. vol. 2. Pergamon; New York: 1990. p. 306..

    1. Trost BM, Madsen R, Guile SD, Brown B. J. Am. Chem. Soc. 2000;122:5947.
    2. Palmer CF, McCague R, Ruecroft G, Savage S, Taylor SJC, Ries C. Tetrahedron Lett. 1996;37:4601.
    3. Li F, Brogan JB, Gage JL, Zhang D, Miller MJ. J. Org. Chem. 2004;69:4538. - PubMed
    1. Goodchild J. In: Topics in Antibiotic Chemistry. Sammes PG, editor. vol. 6B. Wiley; New York: 1982. p. 99.
    1. De Clercq E. Biochem. Pharmacol. 1987;36:2567. - PubMed
    2. Cools M, De Clercq E. Biochem. Pharmacol. 1989;38:1061. - PubMed
    1. Bennett LL, Jr., Brockman RW, Rose LM, Allan PW, Shaddix SC, Shealy YF, Clayton JD. Mol. Pharmacol. 1985;27:666. - PubMed

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