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

Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin. Research Abstract Details 

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

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

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.

Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin. Publishing Authors By Initials

MX Jiang,B Jin,JL Gage,A Priour,G Savela,MJ Miller,

For similar amino acids, peptides, and proteins: amino acids: amino acids, basic: ornithine research abstracts see: amino acids, peptides, and proteins: amino acids: amino acids, basic: ornithine research

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

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: The Journal of organic chemistry

VOLUME: 71

Page Numbers: 4164-9

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 26

MONTH: May

YEAR: 2006

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

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LANGUAGE: eng

NlmUniqueID: 2985193

Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin. Keywords Mesh Terms:

KEYWORDS: Ornithine

MESH TERMS: chemical synthesis

Chemical & Substance for Abstract: Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin. Information

Substance Name: Ornithine

Registry Number: 7006-33-9

Grant and Affiliation Information for Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin.

AFFILIATION: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: R01 GM68012

ACRONYM: GM

MEDLINETA: J Org Chem

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