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Synthesis 2009(8): 1287-1290  
DOI: 10.1055/s-0028-1088039
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Stereoselective Synthesis of Paeonilactone B

Francesco G. Gatti*a, Stefano Serrab
a Dipartimento di Chimica dei Materiali, Ingegneria Chimica ‘G. Natta’ del Politecnico, Via Mancinelli 7, 20131 Milan, Italy
Fax: +39(02)23993080; e-Mail: francesco.gatti@polimi.it;
b CNR- Istituto di Chimica del Riconoscimento Molecolare, Via Mancinelli 7, 20131 Milan, Italy
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Publikationsverlauf

Received 21 August 2008
Publikationsdatum:
25. März 2009 (online)

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Abstract

A new stereoselective synthesis of paeonilactone B has been achieved in ten steps and in 11.5% overall yield starting from the enantiomerically enriched terpenol 2. Key synthetic steps are based on a regioselective metalation and on a regio- and diastereoselective epoxidation.

Key words

natural product - terpene - metalation - homoallylic epoxidation - lactone

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