377090-75-0

Upstream product

• 377090-73-8 (R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 133464-35-4 3-benzyl 4-methyl (4R)-2,2-dimethyloxazolidine-3,4-dicarboxylate 
• 501-53-1 benzyl chloroformate 
• 93204-36-5 (R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate 
• 377090-74-9 1-(1-(benzyloxycarbonylamino)-2-hydroxyethyl)-1-hydroxycyclopropane 

Downstream Products

• 77448-58-9 (S)-cleonin 

Relevant academic research and scientific papers

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.