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A novel approach to the regioselective acylation of spirocyclic C-glucoside of papulacandins

✍ Scribed by Chafiq Hamdouchi; Carlos Jaramillo; Javier Lopez-Prados; Almudena Rubio

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
87 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A novel approach to the regioselective acylation of spirocyclic C-glucoside of papulacandins is reported. Conditions were found to effect regioselective acylation of triol 2 to give 2-O-acyl derivatives (5), which after deprotection with TASF afforded exclusively 2-O-acyl derivatives ( 8). An extensive migration of the acyl group from 2-O-to 3-O-position was observed when the desilylation was conducted with TBAF. These findings provided with a convenient means for extending the SAR of papulacandins at these positions.

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