Synthesis of trans-Fused 3,6-Anhydro Hexofuranose Frameworks via Catalytic Hydrogenolysis Triggered Debenzylative Intramolecular Acetalation

Abstract

Presented herein is the chemical construction of unprecedented 3,4-trans-3,6-anhydro hexofuranose frameworks. The disfavored 3,6-anhydro hexofuranosides were effectively established by Pd-catalyzed debenzylative intramolecular acetalation for the first time. The critical roles of benzyl protection and Pd as catalyst were demonstrated. Various 3,4-trans-3,6-anhydro sugars including sauropunol E was first obtained in satisfactory yields. Pharmaceutical investigation of the sauropunol E and its analogues revealed their potential application as anti-inflammatory agents.

Keywords: 3,4-trans-3,6-anhydro hexofuranose; anti-inflammatory activity; debenzylative intramolecular acetalation; natural products; sauropunols.