Issue 81, 2013
From the journal:

Chemical Communications

Aziridine-based concise synthesis of (±)-alstonerine†

Donald Craig,*a   Frederick W. Goldberg,b   Richard W. Pett,a   Niels T. H. Tholena  and  Andrew J. P. Whitec  

* Corresponding authors

a Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, UK
E-mail: d.craig@imperial.ac.uk
Fax: +44 (0)20 7594 5804
Tel: +44 (0)20 7594 5771

b AstraZeneca, Mereside, Alderley Park, Macclesfield, Cheshire SK10 4TG, UK

c Chemical Crystallography Laboratory, Imperial College London, South Kensington Campus, London SW7 2AZ, UK

Abstract

A concise synthesis of the macroline-related alkaloid (±)-alstonerine is reported. Key steps are regioselective and stereospecific aziridine ring-opening using a sulfone-stabilised carbanion, Me3Al-mediated O → N-transacylation–elimination, intramolecular Michael reaction, and one-pot reduction–dehydration–Pictet–Spengler cyclisation.

Graphical abstract: Aziridine-based concise synthesis of (±)-alstonerine

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Article information

DOI
https://doi.org/10.1039/C3CC45543B
Article type
Communication
Submitted
22 Jul 2013
Accepted
28 Aug 2013
First published
29 Aug 2013

Chem. Commun., 2013,49, 9275-9277

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Aziridine-based concise synthesis of (±)-alstonerine

D. Craig, F. W. Goldberg, R. W. Pett, N. T. H. Tholen and A. J. P. White, Chem. Commun., 2013, 49, 9275 DOI: 10.1039/C3CC45543B

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