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Synthesis 2011(18): 2865-2892
DOI: 10.1055/s-0030-1260168
DOI: 10.1055/s-0030-1260168
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New YorkTotal Synthesis of Polypropionate-Derived γ-Pyrone Natural Products
Further Information
Received
4 May 2011
Publication Date:
10 August 2011 (online)
Publication History
Publication Date:
10 August 2011 (online)
Abstract
Over the years a wide variety of γ-pyrone-containing natural products have been isolated and a number of their total syntheses accomplished. This review discusses a selection of synthetic strategies towards the total synthesis of some of these complex metabolites.
1 Introduction
2 Polyketide Biosynthesis
3 Common Methodology for γ-Pyrone Construction
4 Synthetic Approaches
5 Polyunsaturated γ-Pyrones
5.1 Conjugated Polyenes: Cyercenes and Placidenes
5.2 Non-Conjugated Polyenes: Actinopyrone and Verticipyrone
6 Polyoxygenated Side-Chain
6.1 Baconipyrones A-D, Siphonarins A and B
6.2 Auripyrones A and B
7 Nitrophenyl γ-Pyrones and Derivatives
7.1 Aureothin, N-Acetylaureothamine
8 Electrocyclisation Reactions in γ-Pyrone Natural Product Synthesis
8.1 The Tridachione Family
8.2 The Tridachiahydropyrones
8.3 Spectinabilin and the ‘SNF’ Compounds
9 Conclusions
Key words
γ-pyrones - polyketides - biomimetic synthesis - natural products - electrocyclisation reactions
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