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Issue 0, 1968
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Allenes. Part XIX. Synthesis of (±)-hypoglycin A and configuration of the natural isomer

Abstract

The synthesis of hypoglycin A by way of the allenic intermediate, diethyl 1-formylaminopenta-3,4-diene-1,1-dicarboxylate, by Simmons–Smith methylation, is described. Model experiments with ethyl buta-2,3-dienoate and diethyl allyl(formylamino)malonate gave ethyl methylenecyclopropanecarboxylate and, after hydrolysis and decarboxylation, 2-amino-3-cyclopropylpropionic acid. Degradation of hypoglycin A to (+)-3-methylpentanoic acid of known (S)-configuration establishes the configuration as (+)-(2S : 4S)-2-amino-4,5-methanohex-5-enoic acid.

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J. Chem. Soc. C, 1968, 288-290
Article type
Paper

Allenes. Part XIX. Synthesis of (±)-hypoglycin A and configuration of the natural isomer

D. K. Black and S. R. Landor, J. Chem. Soc. C, 1968, 288
DOI: 10.1039/J39680000288

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