Issue 16, 2004
From the journal:

Organic & Biomolecular Chemistry

Synthesis and solid state conformation of phenylalanine mimetics constrained in a proline-like conformation

James Gardinera  and  Andrew D. Abell*a  

* Corresponding authors

a Department of Chemistry, University of Canterbury, Christchurch, New Zealand
E-mail: andrew.abell@canterbury.ac.nz
Fax: 64-3-3642110
Tel: 64-3-3642818

Abstract

We present the synthesis of five- and six-membered cyclic phenylalanine mimics (1, 9, 16, and 17) that are constrained in a proline-like conformation. The five-membered mimetic 16 was prepared by Ring Closing Metathesis (RCM) of diene 15, itself prepared by α-benzylation of the L-methionine derived oxazolidinone 10, followed by oxidative elimination, ring hydrolysis and N-allylation. The six-membered mimetic 1 was prepared by allylating the L-phenylalanine-derived oxazolidinone 5, followed by hydrolysis, N-allylation and RCM. Olefins 1 and 16 were catalytically hydrogenated to give 9 and 17, respectively. The solid state structures of 9 and 16 were determined by X-ray crystallography and their conformations compared with that of 1.

Graphical abstract: Synthesis and solid state conformation of phenylalanine mimetics constrained in a proline-like conformation

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Article information

DOI
https://doi.org/10.1039/B406450J
Article type
Paper
Submitted
29 Apr 2004
Accepted
11 Jun 2004
First published
27 Jul 2004

Org. Biomol. Chem., 2004,2, 2365-2370

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Synthesis and solid state conformation of phenylalanine mimetics constrained in a proline-like conformation

J. Gardiner and A. D. Abell, Org. Biomol. Chem., 2004, 2, 2365 DOI: 10.1039/B406450J

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