The Stereoselective Synthesis of Neolignans

Michael Sefkow

doi:10.1055/s-2003-42482

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Synthesis 2003(17): 2595-2625
DOI: 10.1055/s-2003-42482

REVIEW

The Stereoselective Synthesis of Neolignans

Michael Sefkow*
Universität Potsdam, Institut für Chemie, Karl-Liebknecht-Straße 24-25, 14476 Golm, Germany.
Fax: +49(331)9775067; e-Mail: sefkow@rz.uni-potsdam.de.;

Further Information

Publication History

Received 5 September 2003
Publication Date:
21 November 2003 (online)

Abstract
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Abstract

Neolignans, dehydrodimers of phenylpropenes, are important natural products with high structural diversity and various biological properties. Several diastereo- and enantioselective synthesis of neolignans have been developed in the past, either specific for each of the various neolignan skeletons or randomized. This review summarizes the efforts towards the synthesis of chiral neolignans, racemic and optically active, and provides a brief outlook for future developments.

1 Introduction
2 8,5′-Neolignans with Dihydrobenzofuran Skeleton
2.1 Diastereoselective Synthesis of Dihydrobenzofuran Neolignans
2.2 Enantioselective Synthesis of Dihydrobenzofuran Neolignans
3 8,3′-Neolignans
4 8,1′-Neolignans
5 8-O-4′-Neolignans
5.1 Diastereoselective Synthesis of 8-O-4′-Neolignans
5.2 Enantioselective Synthesis of 8-O-4′-Neolignans
6 Benzodioxane-Neolignans
6.1 Diastereoselective Synthesis of Benzodioxane-Neolignans
6.2 Enantioselective Synthesis of Benzodioxane-Neolignans
7 Bicyclo[3.2.1]Octane-Neolignans
8 Conclusion and Outlook

Key words

natural products - neolignans - stereoselective synthesis - dihydrobenzofurans - enantioselective synthesis

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CAS-Search from 01.07.2003.

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Sefkow, M. unpublished results.

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The cytotoxicity of 150 and 151 against KB cell cultures was 1,75 and 2,55 µg/mL, respectively. For more details see reference 106.