First stereocontrolled synthesis of (S)-cleonin and related cyclopropyl-substituted amino acids

A Esposito; P P Piras; D Ramazzotti; M Taddei

doi:10.1021/ol016477c

First stereocontrolled synthesis of (S)-cleonin and related cyclopropyl-substituted amino acids

Org Lett. 2001 Oct 18;3(21):3273-5. doi: 10.1021/ol016477c.

Authors

A Esposito¹, P P Piras, D Ramazzotti, M Taddei

Affiliation

¹ Dipartimento di Chimica, Università degli Studi di Sassari, Via Vienna 2, I-07100 Sassari, Italy.

PMID: 11594812
DOI: 10.1021/ol016477c

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis*
Antibiotics, Antineoplastic / chemical synthesis
Bleomycin / analogs & derivatives*
Bleomycin / chemical synthesis
Cyclopropanes / chemical synthesis*
Stereoisomerism

Substances

Amino Acids
Antibiotics, Antineoplastic
Cyclopropanes
Bleomycin
cleonine
cleomycin B2