TOTAL SYNTHESIS OF ACETYLMELODORINOL

An enantioselective total synthesis of bioactive melodorinol and acety lmelodorinol starting from 2,3-O-isopropylidene-D-glyceraldehyde and a n alkoxyfuran is reported. Lithiation of the alkoxyfuran and subsequen t reaction with the glyceraldehyde provided two diastereomers. These t wo adducts were treated with p-toluenesulfonic acid in aqueous THF to give a gamma-propylidene butenolide, which was converted to melodorino l and acetylmelodorinol by acylation. Copyright (C) 1996 Published by Elsevier Science Ltd