A concise diastereoselective synthesis of 5′-epi synargentolide-B

Kumaraswamy, Gullapalli; Raghu, Nimmakayala; Jayaprakash, Neerasa; Ankamma, Kukkadapu

doi:10.1016/j.tet.2015.06.080

Cited by 8 publications

(1 citation statement)

References 33 publications

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“…They also synthesized the enantiomer of natural synargentolide B [66]. A diastereoselective synthesis of 5 -epi-synargentolide B has also been reported [67].…”

Section: Synargentolide Bmentioning

confidence: 99%

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

et al. 2020

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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.

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“…They also synthesized the enantiomer of natural synargentolide B [66]. A diastereoselective synthesis of 5 -epi-synargentolide B has also been reported [67].…”

Section: Synargentolide Bmentioning

confidence: 99%

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

et al. 2020

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The Asymmetric Vinylogous Mukaiyama Aldol Reaction

Cordes

Kalesse

2019

Organic Reactions

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The vinylogous Mukaiyama aldol (VMA) reaction allows efficient access to larger segments for complex natural product synthesis, primarily polyketides, through the construction of vicinal hydroxyl and methyl groups as well as di‐ and tri‐substituted double bonds in a single operation. In this chapter, the current scope and limitations of this transformation, as well as its application in natural product synthesis, are discussed.

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Intertwined Analytical, Experimental and Theoretical Studies on the Formation and Structure of a Copper Dienolate

Lecachey

Palais

Courcy

et al. 2021

Chemistry A European J

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The reaction of a silyl dienolate, a Cu(II) salt and TBAT yielding the corresponding copper dienolate is addressed. A combined NMR and cyclic voltammetry analysis first highlight the role of TBAT in the Cu(II) to Cu(I) reduction and the structure of the precatalytic species. From these first results a second set of NMR and theoretical studies enable the determination of the structure and the mechanism of formation of the copper dienolate catalytic species. Finally, we showed that that the copper catalyst promote the E/Z scis/s-trans equilibration of the silyl dienolate precursor through a copper dienolate intermediate. All of these results unveil some peculiarities of the catalytic and asymmetric vinylogous Mukaiyama reaction.

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A concise diastereoselective synthesis of 5′-epi synargentolide-B

Cited by 8 publications

References 33 publications

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

The Asymmetric Vinylogous Mukaiyama Aldol Reaction

Intertwined Analytical, Experimental and Theoretical Studies on the Formation and Structure of a Copper Dienolate

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