Total Synthesis of Polypropionate-Derived γ-Pyrone
Natural Products

Pallavi Sharma; Kimberley J. Powell; James Burnley; Amani S. Awaad; John E. Moses

doi:10.1055/s-0030-1260168

REVIEW

Total Synthesis of Polypropionate-Derived γ-Pyrone Natural Products

Pallavi Sharma^a, Kimberley J. Powell^a, James Burnley^a, Amani S. Awaad^b, John E. Moses*^a,b
^a School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK
Fax: +44(115)9513564; e-Mail: john.moses@nottingham.ac.uk;
^b Chemistry Department, Faculty of Sciences, King Saud University, Riyadh, Saudi Arabia

Abstract

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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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Referenzen

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