Issue 13, 2003
From the journal:

Organic & Biomolecular Chemistry

Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues†

Muhammed Anwar,a   Jonathan H. Bailey,a   Laura C. Dickinson,a   Hermia J. Edwards,a   Rajesh Goswamia  and  Mark G. Moloney*a  

* Corresponding authors

a The Department of Chemistry, Dyson Perrins Laboratory, The University of Oxford, South Parks Road, Oxford

Abstract

Alkylation reactions using α-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.

Graphical abstract: Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B303924B
Article type
Paper
Submitted
10 Apr 2003
Accepted
13 May 2003
First published
05 Jun 2003

Org. Biomol. Chem., 2003,1, 2364-2376

Permissions

Request permissions

Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues

M. Anwar, J. H. Bailey, L. C. Dickinson, H. J. Edwards, R. Goswami and M. G. Moloney, Org. Biomol. Chem., 2003, 1, 2364 DOI: 10.1039/B303924B

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.

Social activity

Spotlight

Advertisements