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Synthesis 2009(20): 3488-3492  
DOI: 10.1055/s-0029-1216967
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Improved Synthesis of an Ascaroside Pheromone Controlling Dauer Larva Development in Caenorhabditis elegans

René Martina, Tina Schäfera, Gabriele Theumera, Eugeni V. Entchevb, Teymuras V. Kurzchaliab, Hans-Joachim Knölker*a
a Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany
Fax: +49(351)46337030; e-Mail: hans-joachim.knoelker@tu-dresden.de;
b Max-Planck-Institut für Molekulare Zellbiologie und Genetik, Pfotenhauerstraße 108, 01307 Dresden, Germany
Further Information

Publication History

Received 22 June 2009
Publication Date:
21 August 2009 (online)

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Abstract

Using an efficient Wacker oxidation as a key step, we describe a significantly improved synthesis of the dauer-promoting ascaroside 2 for biological studies of the novel sterol ring methylase STRM-1.

Key words

carbohydrates - natural products - pheromones - stereoselective synthesis - Wacker reactions

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