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Synlett 2013; 24(18): 2423-2426
DOI: 10.1055/s-0033-1340084
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Sterically Hindered Chiral 1,4-Diols from Different Lignan-Based Backbones

Yury Brusentsev
a   Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, 20500 Åbo (Turku), Finland   Email: paeklund@abo.fi
,
Mikko M. Hänninen
b   Department of Chemistry, University of Jyväskylä, P.O. Box 35, 40014, Jyväskylä, Finland
,
Patrik Eklund*
a   Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, 20500 Åbo (Turku), Finland   Email: paeklund@abo.fi
› Author Affiliations
Further Information

Publication History

Received: 06 September 2013

Accepted after revision: 14 October 2013

Publication Date:
21 October 2013 (online)

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Abstract

Methods for synthetic modifications of the natural dibenzylbutyrolactone lignan hydroxymatairesinol into chiral 1,4-diols with different lignan-derived backbones have been developed. A stepwise procedure, involving alkylation and oxidation, was shown to be successful and several highly substituted 1,4-diols were prepared. Some substituted butyrolactones resisted alkylation and led to the formation unusually stable hemiketals (butyrolactols). The formation of stable hemiketals was investigated in detail, showing that different backbone structures influence the formation and reactivity of the hemiketals.

Key words

hydroxymatairesinol - chiral 1,4-diols - TADDOL - lignans - burtyrolactol

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information

Primary Data

    for this article are available online at ­http://www.thieme-connect.com/ejournals/toc/synlett and can be cited using the following DOI: 10.4125/pd0051th.
  • Primary Data
 

  • References and Notes

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