ol052866l_si_001.pdf (2.97 MB)
Download fileGeneral Method for Synthesizing Pyranoid Glycals. A New Route to Allal and Gulal Derivatives
journal contribution
posted on 2006-02-16, 00:00 authored by Omar Boutureira, Miguel Angel Rodríguez, M. Isabel Matheu, Yolanda Díaz, Sergio CastillónPyranoid 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.