Elsevier

Tetrahedron Letters

Volume 43, Issue 21, 20 May 2002, Pages 3875-3878
Tetrahedron Letters

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

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Abstract

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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Acknowledgements

This research was supported by the CDTI program (Plan Concertado 96/0036) and the Spanish Farma III program (Ministerio de Industria y Ministerio de Sanidad). We are also grateful to the Lilly Antifungal Action Group for their advice and interest in this work.

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