Synthesis and biology of 1,4-benzodioxane lignan natural products

Covering: up to 2015 Lignan-derived 1,4-benzodioxane natural products have been shown to exhibit a diverse array of biological activities, which has lent them to be the focus of a wealth of synthetic attention. Herein we review the background, bioactivities, biosynthesis and synthetic approaches to...

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Bibliographic Details
Published inNatural product reports Vol. 32; no. 1; pp. 1369 - 1388
Main Authors Pilkington, Lisa I, Barker, David
Format Journal Article
LanguageEnglish
Published England 23.09.2015
Subjects
Biological Products - chemical synthesis
Biological Products - chemistry
Dioxanes - chemical synthesis
Dioxanes - chemistry
Lignans - chemical synthesis
Lignans - chemistry
Molecular Structure
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Summary:Covering: up to 2015 Lignan-derived 1,4-benzodioxane natural products have been shown to exhibit a diverse array of biological activities, which has lent them to be the focus of a wealth of synthetic attention. Herein we review the background, bioactivities, biosynthesis and synthetic approaches to the 1,4-benzodioxane lignan scaffold, with an emphasis on 1,4-benzodioxane oxyneolignans. This review describes the evolution of synthetic methods towards 1,4-benzodioxane lignan natural products, from early biomimetic approaches to recent enantiospecific syntheses. Additionally, a comprehensive report of their biosynthesis and significant biological activities is detailed.
Bibliography:Lisa I. Pilkington was born in Auckland, New Zealand. She graduated in 2010 from the University of Auckland with a BA/BSc conjoint degree majoring in Chemistry, Statistics and German. Lisa then went on to graduate with a BSc (Honours, First Class) in 2011, followed by a PhD in 2015 from the same university under the supervision of Dr David Barker, working on the asymmetric synthesis of 1,4-benzodioxane lignans. She is currently undertaking postdoctoral research with the Auckland Cancer Society Research Centre and the School of Chemical Sciences at the University of Auckland.
David Barker was born in Altrincham, UK. After moving to Australia, he graduated from the University of Sydney with a BSc degree (Honours, First Class) and then completed his PhD in 2002 at the same university. After post-doctoral research at the School of Medical Sciences at the University of New South Wales working with Prof. Larry Wakelin, in 2004 he joined the University of Auckland as a lecturer. He is currently Senior Lecturer in Organic and Medicinal Chemistry and he has a diverse range of synthetic interests including biologically active natural products, drug discovery and development of novel polymeric scaffolds.
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ISSN:0265-0568
1460-4752
DOI:10.1039/c5np00048c