Chiral Models of the Furenone Moiety of Germacranolide Sesquiterpenes

Article abstract of DOI:10.1021/jo01295a047

A procedure is outlined for converting 2,3:5,6-di-O-isopropylidene-D-mannose (4, diacetone mannose), by a series of simple, efficient steps, into the unsaturated hydroxy esters 14 and 15, which are then oxidized by Fetizon's reagent to afford the dienones 3a and 3b, these being analogues of the furenone system found in many germacranolide sesquiterpenes.