A synthesis of rosenonolactone and deoxyrosenonolactone
Abstract
Methyl isocupressate (21) has been transformed with acid into the rosadienoic esters (18) and (19). The 13α-methyl compound (19) was converted via the epoxide (30), into the unsaturated lactone (35), and thence into deoxyrosenonolactone (1) and rosenonolactone (4). Conversion of the synthetic racemic ester (44) into the racemate of ester (28) completes the formal total synthesis of the racemic metabolites.