The Total Synthesis of Eponemycin

Abstract
Eponemycin, an antibiotic with a highly potent and specific antitumor activity against B16 melanoma cells in vivo, has been synthesized. The framework of the western half of the molecule was built up from N-trityl-γ, δ-didehydroleucinal and the dilithium derivative LiO-CH2C(Li)=CH2. In the final step, a vinyl ketone was oxidized nonstereoselectively to give a mixture of three isomers from which eponemycin was isolated in 40% yield.

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