Siebenringe durch Cyclisierungen an Übergangsmetall‐Komplexen: [4+3], [3+2+2] und [5+2]

Butenschön, Holger

doi:10.1002/ange.200801738

Cited by 39 publications

(3 citation statements)

References 59 publications

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“…[1] However, due to unfavorable entropic and enthalpic factors, the synthesis of these compounds through ring-closure reactions remains challenging. [2] Among the various synthetic methodologies to prepare cycloheptane derivatives, cycloaddition routes [2,3] such as [4+3] or [5+2] cycloadditions with transition-metal catalysts, [4,5] have appeared to be competitive.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7‐Membered Carbocycles

Lepronier¹,

Achard²,

Giordano³

et al. 2016

Adv Synth Catal

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International audiencePalladium(II) acetate in association with secondary phosphine oxides provides an efficient catalytic system for [2+1] cycloadditions starting from oxanorbornene derivatives and tertiary propargyl esters giving rise to vinylidenecyclopropanes. This reaction is specific to bidentate phosphinito-phosphinous acid ligands generated from secondary phosphine oxides. The [2+1] cycloaddition was found broad in scope with a high tolerance to various functional groups. Moreover, vinylidenecyclopropanes were straightforwardly converted into oxabicyclo[3.2.1]oct-2-ene derivatives through a palladium-catalyzed ring-expansion. Finally, the oxa bridge cleavage of oxatricyclic compounds allows the obtention of functionalized 7-membered carbocycles

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Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7‐Membered Carbocycles

Lepronier¹,

Achard²,

Giordano³

et al. 2016

Adv Synth Catal

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show abstract

“…However, due to unfavorable entropic and enthalpic factors, the synthesis of these compounds through ring‐closure reactions remains challenging 2. Among the various synthetic methodologies to prepare cycloheptane derivatives, cycloaddition routes2, 3 such as [4+3] or [5+2] cycloadditions with transition‐metal catalysts,4, 5 have appeared to be competitive.…”

Section: Introductionmentioning

confidence: 99%

Characterization of FabG and FabI of the Streptomyces coelicolor Dissociated Fatty Acid Synthase

Singh

Reynolds

2015

ChemBioChem

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Streptomyces coelicolor produces fatty acids for both primary metabolism and for biosynthesis of the secondary metabolite undecylprodiginine. The first and last reductive steps during the chain elongation cycle of fatty acid biosynthesis are catalyzed by FabG and FabI. The S. coelicolor genome sequence has one fabI gene (SCO1814) and three likely fabG genes (SCO1815, SCO1345, and SCO1846). We report the expression, purification, and characterization of the corresponding gene products. Kinetic analyses revealed that all three FabGs and FabI are capable of utilizing both straight and branched-chain β-ketoacyl-NAC and enoyl-NAC substrates, respectively. Furthermore, only SCO1345 differentiates between ACPs from both biosynthetic pathways. The data presented provide the first experimental evidence that SCO1815, SCO1346, and SCO1814 have the catalytic capability to process intermediates in both fatty acid and undecylprodiginine biosynthesis.

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“…Indeed, a part of the field of [5+2] cycloadditions was most recently reviewed in 2007 as a book chapter by Wender et al., who concentrated on metal‐catalyzed higher‐order cycloadditions, covering the literature until the beginning of 2005 2k. This area has also been the subject of parts of several excellent review articles 2l,3. On the other hand, two reviews concentrating on the involvement of oxidopyrylium and pyridinium species in various dipolar cycloadditions have been reported, covering the literature until the beginning of 2007 4.…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in the [5+2] Cycloaddition

Pellissier¹

2011

Adv Synth Catal

211

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The rapid generation of molecular complexity in a relatively easy manner has made the [5 + 2] cycloaddition approach a highly useful tool in the synthesis of a wide number of complex natural products and important biologically active products containing seven-membered rings. Besides the common and highly efficient [5 + 2] cycloadditions of oxidopyrylium and oxidopyridinium ions with p-systems which offer an easy access to a wide range of novel heterocyclic seven-membered ring molecules with a oxygen or nitrogen bridge, and the less employed [5 + 2] photocycloadditions, the metal-catalyzed [5 + 2] cycloadditions have attracted a lot of attention and have become one of the most popular ways of constructing seven-membered ring products. All these cycloadducts can be synthetically manipulated easily toward a number of interesting molecular structures with high potential applications.

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Siebenringe durch Cyclisierungen an Übergangsmetall‐Komplexen: [4+3], [3+2+2] und [5+2]

Abstract: [24,26]

Cited by 39 publications

References 59 publications

Palladium‐Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7‐Membered Carbocycles

Palladium‐Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7‐Membered Carbocycles

Characterization of FabG and FabI of the Streptomyces coelicolor Dissociated Fatty Acid Synthase

Recent Developments in the [5+2] Cycloaddition

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