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Synlett 2008(17): 2617-2620  
DOI: 10.1055/s-0028-1083511
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Formal Synthesis of Leustroducsin B

Joëlle Moïsea, Ravindra P. Sonawanea, Camilla Corsib, Sebastian V. Wendebornb, Stellios Arseniyadis*a, Janine Cossy*a
a Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 Rue Vauquelin, 75231 Paris Cedex 05, France
Fax: +33(1)40794660; e-Mail: stellios.arseniyadis@espci.fr; e-Mail: janine.cossy@espci.fr;
b Syngenta Crop Protection Muenchwilen AG, WST-820.2.15, Schaffhauserstr. 4332 Stein, Switzerland
Further Information

Publication History

Received 2 July 2008
Publication Date:
01 October 2008 (online)

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Abstract

A formal synthesis of leustroducsin B, a potent antitumor compound, is described featuring two key reactions: an olefin cross-metathesis between α-methylene γ-butyrolactone and a terminal olefin to install the C7-C12 carbon backbone, and a highly stereoselective Brown-type pentenylation which sets the syn-relationship between the two substituents at C4 and C5.

Key words

leustroducsins - antitumor - asymmetric pentenylation - ring-closing metathesis - Sharpless dihydroxylation

    References and Notes

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The second diastereomer could not be detected by either ¹H or ¹³C NMR spectroscopy of the crude reaction mixture, thus suggesting a selectivity superior to 95:5.