General method for synthesizing pyranoid glycals. A new route to allal and gulal derivatives

Identifier:  imarina:9284467

Handle: https://hdl.handle.net/20.500.11797/imarina9284467

Authors:  Boutureira, O; Rodríguez, MA; Matheu, MI; Díaz, Y; Castillón, S

Abstract:
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. © 2006 American Chemical Society.