A convenient chiron approach to (4R,5R)-5-hydroxyalkylbutan-4-olides and the corresponding 7-oxa analogues from D-(+)-mannitol via an advanced common precursor: syntheses of (-)-muricatacin, 7-oxa-(-)-muricatacin, (4R,5R)-(-)-5-hydroxy-4-decanolide, and (4R,5R)-(-)-7-oxa-5-hydroxy-4-dodecanolide

An efficient and concise chiron approach toward the synthesis of (-)-muricatacin and its unnatural 7-oxa analogue starting from commercially available and inexpensive D-(+)-mannitol via an advanced common chiral precursor has been described. In addition, (4R,5R)-(-)-5-hydroxy-4-decanolide and (4R,5R)-(-)-7-oxa-5-hydroxy-4-dodecanolide were also synthesized to show the versatility of this synthetic strategy. The methodology involves the conversion of a common chiral intermediate, prepared from D-(+)-mannitol in six steps, to a variety of target molecules in only two steps. (C) 2014 Elsevier Ltd. All rights reserved.