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

Gandavadi Sunilkumar; Dendukuri Nagamani; Narshinha P. Argade; Krishna N. Ganesh

doi:10.1055/s-2003-41075

SHORTPAPER

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

Gandavadi Sunilkumar, Dendukuri Nagamani, Narshinha P. Argade*, Krishna N. Ganesh*
Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)5893153; e-Mail: argade@dalton.ncl.res.in; e-Mail: kng@ems.ncl.res.in;

Abstract

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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

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References

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