The Total Synthesis of Eponemycin

Ulrich Schmidt; Johannes Schmidt

doi:10.1055/s-1994-25464

Synthesis 1994; 1994(3): 300-304
DOI: 10.1055/s-1994-25464

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The Total Synthesis of Eponemycin

Ulrich Schmidt^* , Johannes Schmidt

^*Institut für Organische Chemie und Isotopenforschung der Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany

Abstract

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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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