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General Method for Synthesizing Pyranoid Glycals. A New Route to Allal and Gulal Derivatives

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journal contribution
posted on 2006-02-16, 00:00 authored by Omar Boutureira, Miguel Angel Rodríguez, M. Isabel Matheu, Yolanda Díaz, Sergio Castillón
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.