American Chemical Society
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First Stereocontrolled Synthesis of (S)-Cleonin and Related Cyclopropyl-Substituted Amino Acids

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journal contribution
posted on 2001-09-22, 00:00 authored by Annamaria Esposito, Pier Paolo Piras, Daniela Ramazzotti, Maurizio Taddei
Enantiomerically pure (S)-cleonin, a key component of the antitumor antibiotic cleomycin, was prepared starting from (R)-serine. The Kulinkovich cyclopropanation of the methyl ester of N-Cbz serine acetonide gave the hydroxycyclopropyl moiety. The amino alcohol region was further oxidized to amino acid. The Kulinkovich cyclopropanation allowed also the preparation of other non-natural substituted cyclopropylglycines.