Synthesis of 2-(Mannopyranosyloxy methyl) Benzo[b] furan through Sonogashira Coupling and Intramolecular Dehydrocyclization

In recent years, benzo-fused cyclic ether skeletons have received increasing interest,1 mainly due to their presence in a wide variety of natural products with promising

Experimental Methods ........................................................................................... 130 General Methods ............................................................................................... 130 2-(2,3,4,6-Tetra-O-acetyl-α-d-mannopyranosyloxymethyl) benzo[b]furan (2) .......................................................................................... 130

Acknowledgments .................................................................................................. 131 References .............................................................................................................. 132

In our ongoing research efforts to improve and develop new mannosides with promising bioactivities,4,5 we describe herein the synthesis of mannopyranoside 2 from prop-2-ynyl 2,3,4,6-tetra-O-acetyl-α-d-mannopyranoside 16 and 2-iodophenol using a tandem Sonogashira cross coupling and intramolecular dehydrocyclization reactions.