Issue 14, 2008
From the journal:

Organic & Biomolecular Chemistry

Stereochemistry and rearrangement reactions of hydroxylignanolactones†‡

Barbara Raffaelli,a   Monika Pohjoispää,a   Tapio Hase,a   Christine J. Cardin,b   Yu Ganb  and  Kristiina Wähälä*a  

* Corresponding authors

a Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, P.O. Box 55, Finland
E-mail: kristiina.wahala@helsinki.fi.
Fax: +358 9191 50357
Tel: +358 9191 50356

b Department of Chemistry, University of Reading, Whiteknights, Reading, UK
E-mail: c.j.cardin@rdg.ac.uk.
Fax: +44 118 3786331
Tel: +44 118 3788215

Abstract

Various conflicting data on the rearrangement and absolute stereochemistry of hydroxylignano-9,7′-lactones are resolved using 18O labeled compounds, also confirmed by an X-ray analysis of a pure lignano-9,7′-lactone enantiomer, obtained for the first time. Under NaH/DMF rearrangement conditions a silyl protected hydroxylignano-9,9′-lactone underwent an unexpected silyl migration.

Graphical abstract: Stereochemistry and rearrangement reactions of hydroxylignanolactones

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Article information

DOI
https://doi.org/10.1039/B801593G
Article type
Paper
Submitted
29 Jan 2008
Accepted
11 Apr 2008
First published
19 May 2008

Org. Biomol. Chem., 2008,6, 2619-2627

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Stereochemistry and rearrangement reactions of hydroxylignanolactones

B. Raffaelli, M. Pohjoispää, T. Hase, C. J. Cardin, Y. Gan and K. Wähälä, Org. Biomol. Chem., 2008, 6, 2619 DOI: 10.1039/B801593G

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