Enantiospecific syntheses of aristeromycin and neplanocin A

MS Wolfe, BL Anderson, DR Borcherding…

文献索引：Wolfe, Michael S.; Anderson, Blake L.; Borcherding, David R.; Borchardt, Ronald T. Journal of Organic Chemistry, 1990 , vol. 55, # 15 p. 4712 - 4717

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被引用次数: 59

摘要

The carbocyclic nucleosides (-)-aristeromycin and (-)-neplanocin A were made enantiospecifically in nine steps and ten steps, respectively, from D-ribonic acid y-lactone. Quenching of an organocuprate conjugate addition reaction with either acetic acid or methanesulfinyl chloride determines whether the divergent synthetic route branches toward (-)-aristeromycin or (-)-neplanocin A. An alternate synthesis of cyclopentenone 1, a ...