TOTAL SYNTHESIS OF DL-CERULENIN

A general route to endocyclic α,β-epoxy-γ-butyrolactones is described. The α,β-epoxylactones are potential protein cross-linking agents based upon the spectrum of reactivity displayed with amines and thiolate anion. The epoxylactone 8 is prepared from l-bromo-2-butyne and serves as the key intermediate in a total synthesis of cerulenin (1), an important substance for the study of the enzyme systems involved in fatty acid biosynthesis.© 1979, American Chemical Society. All rights reserved.