The first enantioselective synthesis of the amino acid, (2S,3S,4R)-gamma-hydroxyisoleucine using a palladium(II) catalysed 3,3-sigmatropic rearrangement

Andrew G Jamieson; Andrew Sutherland; Christine L Willis

doi:10.1039/b401076k

The first enantioselective synthesis of the amino acid, (2S,3S,4R)-gamma-hydroxyisoleucine using a palladium(II) catalysed 3,3-sigmatropic rearrangement

Org Biomol Chem. 2004 Mar 21;2(6):808-9. doi: 10.1039/b401076k. Epub 2004 Feb 19.

Authors

Andrew G Jamieson¹, Andrew Sutherland, Christine L Willis

Affiliation

¹ Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, UK G12 8QQ. [email protected]

PMID: 15007405
DOI: 10.1039/b401076k

Abstract

A synthetic route towards the synthesis of (2S,3S,4R)-gamma-hydroxyisoleucine, the amino acid component of the natural product, funebrine has been developed using as the key step, a palladium(II) catalysed 3,3-sigmatropic rearrangement to create the (2S)-stereogenic centre.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis*
Amino Acids / pharmacology
Catalysis
Isoleucine / analogs & derivatives*
Isoleucine / chemical synthesis*
Isoleucine / pharmacology
Lactones / chemistry*
Molecular Structure
Palladium / chemistry*
Pyrroles / chemistry*
Stereoisomerism

Substances

Amino Acids
Lactones
Pyrroles
funebrine
Isoleucine
(2S,3S,4R)-gamma-hydroxyisoleucine
Palladium