Issue 0, 1968

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.

Article information

Article type
Paper

J. Chem. Soc. C, 1968, 288-290

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements