Abstract

The present review summarizes the recent progresses in the synthesis of 2-pyrones and the application to the synthesis of marine natural products. Especially, much attention was placed on the transition metal catalyzed synthetic methodologies in this review.

Highlights

  • Pyrones constitute a family of six-membered unsaturated cyclic compounds containing an oxygen atom

  • 2-pyrone is extremely prevalent in numerous natural products isolated from plants, animals, marine organisms, bacteria, fungi, and insects that exhibit a broad range of biological activities, such as antifungal, antibiotic, cytotoxic, neurotoxic and phytotoxic(Figure 2) [4]

  • For all its importance in organic chemistry and medicinal chemistry, it was not until recently that various transition metal-catalyzed methods for the efficient synthesis of 2-pyrone have been developed and we were able to have a clear understanding of the exact nature and the unique chemical behavior of 2-pyrone

Read more

Summary

Introduction

Pyrones constitute a family of six-membered unsaturated cyclic compounds containing an oxygen atom. In view of chemical motifs, γ-pyrone is the vinylogous form of α-pyrone (instead of α-pyrone, the term “2-pyrone” will be used hereafter), which possesses a lactone. As a result, these ring systems share similar chemical properties (Figure 1) [1,2,3]. For all its importance in organic chemistry and medicinal chemistry, it was not until recently that various transition metal-catalyzed methods for the efficient synthesis of 2-pyrone have been developed and we were able to have a clear understanding of the exact nature and the unique chemical behavior of 2-pyrone. The present review will be concerned with the recent advances in the synthesis of 2-pyrones with a special emphasis on metal-catalyzed methods, but other significant methods will be covered as well as the synthesis of complex marine natural products

Palladium-Catalyzed Synthesis of 2-Pyrones
Gold-Catalyzed Cyclo-Isomerization Strategy
Rhodium-Catalyzed Synthesis of 2-Pyrones
Ruthenium-Catalyzed Synthesis of 2-Pyrones
Nickel-Catalyzed Synthesis of 2-Pyrones
Phosphine-Catalyzed Synthesis of 2-Pyrones
Synthesis of 2-Pyrones via Iodolactonization
Synthesis of 2-Pyrones via Baylis-Hillman Reaction
Ring Expansion Strategy
Condensation
Rearrangement-Cyclization Strategy
Synthetic Application of Substituted 2-Pyrones
Synthetic Application of 4-Bromo-6-Methyl-2-Pyrone
Conclusions
Full Text
Published version (Free)

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call