TOTAL SYNTHESIS OF RACEMIC AVENACIOLIDE

A stereospecific total synthesis of racemic avenaciolide (1) has been realized in 64% overall yield starting from 5-n-octyl-2(5H)-furanone (3). The salient features of this synthesis include stereospecific substitution of both the β and α positions of 3 via a conjugate addition-halogenation sequence, and transformation of an α-methyl-α-tniomethylbutyrolactone into an α-methylene butyrolactone. The anion derived from ethyl propiolate has been utilized for the efficient synthesis of several 5-substituted 2(5H)-furanones. © 1979, American Chemical Society. All rights reserved.