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Synthesis 2009(22): 3775-3784  
DOI: 10.1055/s-0029-1217021
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Investigation of a Unified Strategy for the Synthesis of Anatoxin Analogues: Scope and Limitations

Stephen J. Roea, David L. Hughesa, Pooja Aggarwalb, Robert A. Stockman*a,b
a School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, NR4 7TJ, UK
b School of Chemisty, University of Nottingham, Nottingham, NG7 2RD, UK
e-Mail: Robert.Stockman@Nottingham.ac.uk;
Further Information

Publication History

Received 11 June 2009
Publication Date:
23 September 2009 (online)

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Abstract

Syntheses of the potent neurotoxins and biochemical probes anatoxin-a and homoanatoxin and several analogues by a combined two-directional synthesis-tandem reaction strategy are presented. Key steps include an oxidative desymmetrisation and a tandem Michael-intramolecular Mannich cyclisation.

Key words

anatoxin - homoanatoxin - two-directional - tandem - cascade - Michael - iminium - desymmetrisation

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A table of conditions screened is provided in the supporting information.