Ex Chiral Pool Synthesis of (-)-Siphonarienone from a Methyl-Branched Wax Ester

Yana Galeyeva; Michael Morr; Sabine Laschat; Angelika Baro; Manfred Nimtz; Florenz Sasse

doi:10.1055/s-2005-872205

PAPER

Ex Chiral Pool Synthesis of (-)-Siphonarienone from a Methyl-Branched Wax Ester

Yana Galeyeva^a, Michael Morr^b, Sabine Laschat*^a, Angelika Baro^a, Manfred Nimtz^b, Florenz Sasse^b
^a Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
^b Gesellschaft für Biotechnologische Forschung, Mascheroder Weg 1, 38124 Braunschweig, Germany
e-Mail: sabine.laschat@oc.uni-stuttgart.de;

Abstract

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Abstract

Both optically pure siphonarienal (-)-1 and siphonarienone (-)-2 are accessible from the enantiopure precursor methyl (2R,4R,6R,8R)-2,4,6,8-tetramethylundecanoate 5. The latter was converted into the corresponding methyl 2-undecenoate 9 which either provided aldehyde (-)-1 by reduction and subsequent Swern oxidation of the unsaturated alcohol 10 or gave ketone (-)-2 via Weinreb amide 11 and its conversion with EtMgBr. Alternatively, ketone 2 can be obtained from siphonarienal (-)-1 in a two-step reaction.

Key words

siphonarienes - polypropionates - ex chiral pool synthesis

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References

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