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Synthesis 2004(6): 811-827  
DOI: 10.1055/s-2004-816010
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Furofuran Lignans

Richard C. D. Brown*a, Nigel A. Swainb
a School of Chemistry, University of Southampton, Highfield, Southampton S017 1BJ, UK
Fax: +44(23)80596805; e-Mail: rcb1@soton.ac.uk;
b Pfizer Ltd., Ramsgate Road, Sandwich, Kent CT13 9NJ, UK
Further Information

Publication History

Received 12 February 2004
Publication Date:
15 March 2004 (online)

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Abstract

This review covers synthetic routes to lignans belonging to the 2,6-disubstituted dioxabicyclo[3.3.0]octane subclass (also known as furofurans). The different approaches have been loosely categorised according to the synthetic strategies applied. The routes discussed range from the classical biomimetic oxidative coupling of cinnamyl derivatives to more recent asymmetric syntheses.

1 Introduction

2 Synthetic Routes to Furofurans

2.1 Oxidative Dimerisation of Cinnamyl Alcohols and Cinnamic Acids and Enolate Anions

2.2 Approaches Based on Conjugate Addition of Acyl Anion Equivalents

2.3 Approaches Based on Aldol Chemistry

2.4 Approaches Based on Cycloaddition/Rearrangement

2.5 Radical and Photochemical Strategies

2.6 Transition Metal Mediated Strategies

3 Concluding Remarks

Key words

total synthesis - natural products - furans - ring closure - bicyclic compounds