Synlett 2007(12): 1881-1884  
DOI: 10.1055/s-2007-984521
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the Core Structure of the Cyclocitrinols via SmI2-Mediated Fragmentation of a Cyclopropane Precursor

Sherif El Sheikh, Aike Meier zu Greffen, Johann Lex, Jörg-Martin Neudörfl, Hans-Günther Schmalz*
Institut für Organische Chemie, Universität zu Köln, Greinstr. 4, 50939 Köln, Germany
Fax: +49(221)4703064; e-Mail: schmalz@uni-koeln.de;
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Publikationsverlauf

Received 26 April 2007
Publikationsdatum:
25. Juni 2007 (online)

Abstract

The first synthetic entry towards the cyclocitrinols, a new class of natural products possessing a steroid-analogue structure with a characteristic bicyclo[4.4.1]undecane AB ring system, was elaborated. In the key step, a cyclopropanated intermediate (prepared from dehydroepiandrosterone) was subjected to reductive fragmentation (using SmI2 in THF).