Issue 4, 2007
From the journal:

Organic & Biomolecular Chemistry

Taking control of P1, P1′ and double bond stereochemistry in the synthesis of Phe-Phe (E)-alkene amide isostere dipeptidomimetics†

Daniel Wikteliusa  and  Kristina Luthman*a  

* Corresponding authors

a Department of Chemistry, Medicinal Chemistry, Göteborg University, Göteborg, Sweden
E-mail: luthman@chem.gu.se
Fax: +46 31 7723840
Tel: +46 31 7722894

Abstract

A protocol for the stereocontrolled independent preparation of both C-2 epimers of Phe-Phe trans-vinyl amide isostere dipeptidomimetics has been devised based on a Wittig-type reaction, in which two chiral building blocks were joined with excellent E-selectivity to give compounds of the type PheΨ[(E)-CH[double bond, length as m-dash]CH]-PheOH.

Graphical abstract: Taking control of P1, P1′ and double bond stereochemistry in the synthesis of Phe-Phe (E)-alkene amide isostere dipeptidomimetics

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Article information

DOI
https://doi.org/10.1039/B616906F
Article type
Communication
Submitted
20 Nov 2006
Accepted
01 Dec 2006
First published
14 Dec 2006

Org. Biomol. Chem., 2007,5, 603-605

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Taking control of P1, P1′ and double bond stereochemistry in the synthesis of Phe-Phe (E)-alkene amide isostere dipeptidomimetics

D. Wiktelius and K. Luthman, Org. Biomol. Chem., 2007, 5, 603 DOI: 10.1039/B616906F

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