Synthesis ( IF 2.2 ) Pub Date : 2017-12-20 , DOI: 10.1055/s-0036-1591732 Chris Meier 1 , Simon Weising 1 , Ilaria Torquati 1, 2
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Abstract
Herein we disclose an efficient strategy for the convergent synthesis of 1′,2′-cis-disubstituted carbocyclic ribo-nucleoside analogues. Starting from an enantiomerically pure cyclopentenol precursor, the key step for the preparation of the highly functionalized carbocyclic building block is an asymmetric dihydroxylation. Employing different variants of the Mitsunobu protocol, the condensation with all-natural nucleobases or their precursors affords a series of ribo-configured carbocyclic 1′,2′-cis-disubstituted nucleoside analogues.
Herein we disclose an efficient strategy for the convergent synthesis of 1′,2′-cis-disubstituted carbocyclic ribo-nucleoside analogues. Starting from an enantiomerically pure cyclopentenol precursor, the key step for the preparation of the highly functionalized carbocyclic building block is an asymmetric dihydroxylation. Employing different variants of the Mitsunobu protocol, the condensation with all-natural nucleobases or their precursors affords a series of ribo-configured carbocyclic 1′,2′-cis-disubstituted nucleoside analogues.
中文翻译：
立体选择性合成1'，2'-顺式双取代碳环核糖核苷类似物
摘要
本文中，我们公开了一种有效合成1'，2'-顺式-双取代的碳环核糖-核苷类似物的有效策略。从对映体纯的环戊烯醇前体开始，制备高度官能化的碳环结构单元的关键步骤是不对称二羟基化。利用Mitsunobu方案的不同变体，与全天然核碱基或其前体的缩合提供一系列核糖构型的碳环1'，2'-顺式-双取代核苷类似物。
本文中，我们公开了一种有效合成1'，2'-顺式-双取代的碳环核糖-核苷类似物的有效策略。从对映体纯的环戊烯醇前体开始，制备高度官能化的碳环结构单元的关键步骤是不对称二羟基化。利用Mitsunobu方案的不同变体，与全天然核碱基或其前体的缩合提供一系列核糖构型的碳环1'，2'-顺式-双取代核苷类似物。
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