General method for synthesizing pyranoid glycals.: A new route to allal and gulal derivatives
General method for synthesizing pyranoid glycals.: A new route to allal and gulal derivatives
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DOI：
10.1021/ol052866l
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发表时间：
2006-02-16
期刊：
影响因子：
5.2
通讯作者：
Castillón, S
中科院分区：
文献类型：
--
作者：
Boutureira, O;Rodríguez, MA;Castillón, S
所有构型的吡喃糖醛都可以通过烯化-环化-消除顺序从戊糖获得。在自由基条件下或使用常见的还原剂（如 Zn/Cu、TiCl4/LiAlH4 或萘化锂）可以以优异的产率进行消除。所提出的方法适用于具有allo或gulo构型的糖醛的合成，因为环化步骤对于这些底物更有效。
Pyranoid glycals of all configurations can be obtained from pentoses through an olefination-cyclization-elimination sequence. The elimination can be carried out with excellent yields under radical conditions or by using common reductive reagents such as Zn/Cu, TiCl4/LiAlH4, or lithium naphthalenide. The proposed method is appropriate for the synthesis of glycals with allo or gulo configurations because the cyclization step is more efficient for these substrates.