Synthesis of Marine Natural Product (2S,5S)-Pyrrolidine-2,5-dicarboxylic Acid [1]

Abstract

A five-step synthesis of marine natural product (2S,5S)-pyrrolidine-2,5-dicarboxylic acid (1) has been described starting from methyl ester of BOC-protected (S)-proline via stereoselective electrochemical oxidation with introduction of the methoxy group at C₅-position by S_N2-substitution of the cyano group followed by hydrolysis in 13% overall yield.

Keywords

(S)-proline - stereoselective oxidation - (2S,5S)-pyrrolidine-2,5-dicarboxylic acid - natural product synthesis

1

NCL Communication No. 6648.

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1

NCL Communication No. 6648.

14

The stereochemical assignments are based on the optical rotation of the known compounds.