652135-30-3Relevant academic research and scientific papers
A New Route for the Total Synthesis of 6,7-Dihydroeponemycin
Bennacer, Bibia,Rivalle, Christian,Grierson, David S.
, p. 4569 - 4574 (2007/10/03)
A new synthesis of dihydroeponemycin (2), a peptide epoxide with potent cytotoxic and antiangiogenesis activity, has been developed. In the initial steps, Fmoc-Leu-Cl was converted into the key amino ketone intermediate 9 by Stille coupling with tributylvinyltin, conjugate addition of PhSA1Me 2 to the derived enone, S-oxidation, and heat-induced syn elimination. Subsequent reaction of 9 with H2O2 and catalytic Triton B produced the corresponding epoxides as a 1:1 diastereomeric mixture in 89 % yield. These epoxides were separated and individually converted into 2 and(2S)-epi-dihydroeponemycin (24) in a four-step "one-pot" protocol (77 % overall yield in both cases). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
