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

P.-   Q.   Huang; W.-   H.   Meng

doi:10.2174/1570178043488626

Abstract

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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Letters in Organic Chemistry

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

Volume: 1 Issue: 1

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

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

Abstract: 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.

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Huang Q. P.- and Meng H. W.-, A New Approach to (2S, 3S, 4S)-3-Hydroxy-4-Methylproline, A Subunit in Echinocandin B and Related Oligopeptide Antibiotics, Letters in Organic Chemistry 2004; 1 (1) . https://dx.doi.org/10.2174/1570178043488626