Issue 38, 2013
From the journal:

Organic & Biomolecular Chemistry

Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides†

Jonathan Day,a   Maliha Uroos,a   Richard A. Castledine,a   William Lewis,a   Ben McKeever-Abbasb  and  James Dowden*a  

* Corresponding authors

a School of Chemistry, University of Nottingham, University Park, Nottingham, UK
E-mail: james.dowden@nottingham.ac.uk
Fax: +44 (0)115 9513565
Tel: +44 (0)115 9513566

b Pharmaceutical Development, AstraZeneca, Silk Road Business Park, Macclesfield, UK

Abstract

Cycloaddition reactions between pyridinium ylides and 3-alkenyl oxindoles that proceed in high yield and with very good regio- and diastereoselectivity are reported. The resulting cycloadducts have the same stereochemistry of biologically active oxindole alkaloids, such as strychnofoline.

Graphical abstract: Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides

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Article information

DOI
https://doi.org/10.1039/C3OB41415A
Article type
Paper
Submitted
09 Jul 2013
Accepted
15 Aug 2013
First published
15 Aug 2013
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2013,11, 6502-6509

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Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides

J. Day, M. Uroos, R. A. Castledine, W. Lewis, B. McKeever-Abbas and J. Dowden, Org. Biomol. Chem., 2013, 11, 6502 DOI: 10.1039/C3OB41415A

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