First stereocontrolled synthesis of (S)-cleonin and related cyclopropyl-substituted amino acids.
[reaction: see text]. 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.
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Dipartimento di Chimica, Università degli Studi di Sassari, Via Vienna 2, I-07100 Sassari, Italy.
Piras
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Ramazzotti
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Taddei
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D000596:Amino Acids / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis; D001761:Bleomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003521:Cyclopropanes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000596:Amino Acids; D000903:Antibiotics, Antineoplastic; D003521:Cyclopropanes; D001761:Bleomycin; C448620:cleonine; C027447:cleomycin B2