取代环戊烯的底物依赖性二羟基化反应：用于碳环型西奈芬净和去甲阿司米星的合成
Substrate-dependent dihydroxylation of substituted cyclopentenes: toward the syntheses of carbocyclic sinefungin and noraristeromycin.
作者信息
Jiang May Xiao-Wu, Jin Bohan, Gage Jennifer L, Priour Alain, Savela Gordon, Miller Marvin J
机构信息
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA.
出版信息
J Org Chem. 2006 May 26;71(11):4164-9. doi: 10.1021/jo060224l.
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.
摘要
碳环核苷对于新型治疗药物的开发具有相当大的吸引力。许多此类核苷类似物制备中的关键反应是适当取代的环戊烯的二羟基化反应。尽管通常被认为是常规反应，但在本文中，我们报道了取代基对二羟基化反应面选择性的显著影响。取代的环戊烯底物源自环戊二烯的酰基亚硝基环加成反应，随后进行N-O还原和高效的酶法拆分。这些结果直接用于一种非常高效的抗病毒碳环核苷诺拉霉素5的不对称合成。向碳环辛弗宁7合成的拓展证明了认识到二羟基化反应对取代基的依赖性的重要性。
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