A New Approach to (2S, 3S, 4S)-3-Hydroxy-4-Methylproline, A Subunit in Echinocandin B and Related Oligopeptide Antibiotics

Author(s): P.- Q. Huang, W.- H. Meng.

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 1 , 2004

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A new approach to two protected forms of (2S, 3S, 4S)-3-hydroxy-4-methylproline, a constituent of echinocandins and related oligopeptide antibiotics is reported. The method features a highly regioselective and diastereoselective reductive furylation of protected (2S, 3S)-3-methylmalimide and a chemoselective oxidative transformation of furyl to carboxyl as the key steps.

Keywords: proline, regioselectivity, addition, asymmetric synthesis, malic acid, echinocandins, furan, organometallics

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Article Details

Year: 2004
Page: [99 - 101]
Pages: 3
DOI: 10.2174/1570178043488626

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