Abstract: A stereospecific total synthesis of racemic avenaciolide (1) has been realized in 64% overall yield starting from 5-n-octyL2 (5H)-furanone (3). The salient features of this synthesis include stereospecific substitution of both the@ and (Y positions of 3 via a conjugate addition-halogenation sequence. and transformation of an tu-methyl-tu- thiomethylbutyrolactone into an cu-methylene butyrolactone. The anion derived from ethyl ...
