An Asymmetric Synthesis of (+)-Erysotramidine

Alexander J. Blake; Christopher Gill; Daniel A. Greenhalgh; Nigel S. Simpkins; Fengzhi Zhang

doi:10.1055/s-2005-918478

PAPER

An Asymmetric Synthesis of (+)-Erysotramidine

Alexander J. Blake, Christopher Gill, Daniel A. Greenhalgh, Nigel S. Simpkins*, Fengzhi Zhang
School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK
e-Mail: nigel.simpkins@nottingham.ac.uk; Fax: +44(115)9513564;

Abstract

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Abstract

A new asymmetric total synthesis of the erythrinan alkaloid erysotramidine is described, which uses chiral base desymmetrisation, N-acyliminium addition, and 6-exo-trig radical cyclisation as the key steps.

Key words

alkaloid - asymmetric synthesis - radical reaction - chiral base - erythrinan

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Our specific rotation data for 15 and 2 are not as high as those recorded previously, even taking into account that our material is ca. 92% ee. We attribute this to the presence of extremely low levels of highly optically active contaminants formed following the SeO₂ oxidation.

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