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Synthesis 2009(18): 3061-3066  
DOI: 10.1055/s-0029-1216918
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Studies on the C22-C23 Aldol Coupling of Spirangien

Michael Lorenz, Nadine Bluhm, Markus Kalesse*
Leibniz Universität Hannover, Institut für Organische Chemie, Schneiderberg 1b, 30167 Hannover, Germany
Fax: +49(511)7623011; e-Mail: Markus.Kalesse@oci.uni-hannover.de;
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Publication History

Received 5 March 2009
Publication Date:
23 July 2009 (online)

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Abstract

The aldol reaction is one of the most powerful and versatile methods in polyketide synthesis. Nevertheless, the subtle directing effects remain very often obscure and impede complex natural products syntheses. Here, we report studies on the pivotal aldol coupling employed in the spirangien synthesis. We identified conditions for the stereoselective formation of both stereoisomers in the C22-C23 aldol juncture of spirangien.

Key words

aldol reaction - methyl ketone - natural products - 1,4-induction - Felkin product - Cornforth model

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