Abstract

Pyranone natural products have attracted great attention in recent years from chemists and biologists due to their fascinating stereoisomeric structural features and impressive bioactivities. A large number of stereoselective total syntheses of these compounds have been described in the literature. The natural pyranones with long side chains have recently received significant importance in the synthetic field. In the present article, we aim to review the modern progress of the stereoselective total syntheses of these natural pyranones containing long-chain substituents.

Highlights

  • Pyranones are an important class of natural products [1]

  • We have described the recent progress of the total syntheses of these natural pyranones

  • In a tandem ring-closing/cross-metathesis approach the synthesis of synargentolide

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Summary

Introduction

Pyranones are an important class of natural products [1]. Several natural pyranones have been found to contain long side chains. The side chain is generally present at the C-6 portion of the pyranone ring These naturally occurring pyranones with long-chain substituents have recently drawn considerable attention from the scientific community due to their impressive structural characteristics as well as interesting biological activities. Double bond while spicigerolide has a (Z)-double bond in their respective side chains [3][5] The bioactivity of this class of compounds is promising. Various modern synthetic approaches have been applied to construct the natural pyranone molecules with proper stereostructures. We have described the recent progress of the total syntheses of compounds having long side chains. We have focused our discussion on the total syntheses of molecules, which have repeatedly been constructed by applying various modern synthetic protocols. In recent years,Total different research groups utilized various efficient procedures for the stereoselective

Stereoselective
Dodoneine
Reagents and conditions:
14. The latter and product was treated with to form the aldehyde
Reagents
Reagents and 2conditions:
Rugulactone
61 The wasesterification reacted with of vinyl magnesium bromide and
63. This of aldehyde
77. This alcohol
Synargentolide A
19. Reagents
Synargentolide B
22. Reagents conditions:
23. Reagents
Synrotolide
Ballyl furnished thewith
Cl22Cl
26. Reagents and conditions:
Lippialactone
Cryptofolione
Passifloricin A
2.10. Strictifolione
Conclusions

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