Total synthesis of penta-Me amurensin H and diptoindonesin G featuring a Rh-catalyzed carboacylation/aromatization cascade enabled by C C activation

Qin, Yuting; Zhan, Jun-Ling; Shan, Tiantian; Xu, Tao

doi:10.1016/j.tetlet.2019.02.040

Cited by 13 publications

(6 citation statements)

References 42 publications

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“…When the pendent alkene moiety is replaced with an α-alkoxycarbonyl group, the carbonyl group is inserted and the following aromatization-driven elimination gives rise to benzofurans (Scheme ). This method was applied to the total synthesis of biologically relevant benzofuran natural products …”

Section: Cyclobutanonesmentioning

confidence: 99%

“…110 This method was applied to the total synthesis of biologically relevant benzofuran natural products. 111 In addition to rhodium catalysis, a cobalt-catalyzed alkyne insertion reaction was also reported (Scheme 57). 112 It allows the use of α,α-disubstituted benzocyclobutenone 233 as the substrate, which fails to react with rhodium catalysts.…”

Section: Miscellaneousmentioning

confidence: 99%

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Cleavage of Carbon–Carbon σ-Bonds of Four-Membered Rings

2020

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This article reviews synthetic transformations involving cleavage of a carbon− carbon bond of a four-membered ring, with a particular focus on the examples reported during the period from 2011 to the end of 2019. Most significant is the progress of catalytic reactions involving oxidative addition of carbon−carbon bonds onto transition metals or β-carbon elimination of transition metal alkoxides. When they are looked at from synthetic perspectives, they offer unique and efficient methods to build complex natural products and structures that are difficult to construct by conventional methods. On the other hand, β-scission of radical intermediates has also attracted increasing attention as an alternative elementary step to cleave carbon−carbon bonds. Its site-selectivity is often complementary to that of transition metalcatalyzed reactions. In addition, Lewis acid-mediated and thermally induced ring-opening of cyclobutanone derivatives has garnered renewed attention. On the whole, these examples demonstrate unique synthetic potentials of structurally strained four-membered ring compounds for the construction of organic skeletons.

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Section: Cyclobutanonesmentioning

confidence: 99%

Section: Miscellaneousmentioning

confidence: 99%

Cleavage of Carbon–Carbon σ-Bonds of Four-Membered Rings

2020

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“…All commercially available reagents were used as received. Compounds 1a, 23 2c, 24 2d, 25 7, 26 8, 26 9, 27 and 15 11 were prepared according to the literature.…”

Section: Special Topic Synthesismentioning

confidence: 99%

Tandem Nickel-Catalyzed Dimerization/(4+2) Cycloaddition of Terminal Alkynes with Four-Membered Ring Ketones

Barday¹,

Nicolas²,

Higginson³

et al. 2021

Synthesis

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Controlling the behaviour of terminal alkynes in metal-catalysed intermolecular tandem reactions is a formidable challenge despite the potential advantage offered by these strategies in modern synthesis. Herein, we describe that a nickel catalyst enables a tandem consisting in the rapid dimerization of terminal alkynes into 1,3-enynes and the cycloaddition of these intermediates with an azetidinone, an oxetanone and benzocyclobutenones. Significantly, the slow or sequential additions of reagents and catalysts is not required to orchestrate their reactivity. These results are in stark contrast with previous cycloadditions of terminal alkynes with those strained four-membered ring substrates, which previously led to oligomerization or cyclotrimerization, except in the case of tert-butylacetylene.

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“…3,5-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-ol (7). 8 To a flamedried flask was added anhydrous THF under a nitrogen atmosphere. The solvent was cooled at 0 °C, and n-BuLi (2.5 M in hexanes, 8.0 mL, 37.5 mmol) was added dropwise, then warmed to room temperature, and stirred for 16 h to generate the acetaldehyde lithium enolate (CH 2 �CH−OLi).…”

Section: ■ Conclusionmentioning

confidence: 99%

En Route to Furan-Fused Naphthopyrones: Formal Synthesis of the (+)-Lasionectrin and Its C12-Epimer

López-Mendoza,

Porras-Santos,

Pérez-Bautista

et al. 2023

J. Org. Chem.

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Despite the vast presence of the furan-fused naphthopyrone (FFN) skeleton in many bioactive natural products, such as lasionectrin, at present, a general approach to FFNs has not been developed yet. For that reason, a simple and straightforward synthetic approach consisting of a sequential procedure of a Diels–Alder reaction between 1,3-dimethoxy-benzocyclobutenol I and furan-fused-α,β-unsaturated-δ-lactones II (via an ο-quinodimethane intermediate III ) followed by an oxidative aromatization of the corresponding Diels–Alder adduct IV is reported. Subsequently, the formal synthesis of the (+)-lasionectrin and its C12-epimer was achieved, the latter in only six steps.

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Total synthesis of penta-Me amurensin H and diptoindonesin G featuring a Rh-catalyzed carboacylation/aromatization cascade enabled by C C activation

Cited by 13 publications

References 42 publications

Cleavage of Carbon–Carbon σ-Bonds of Four-Membered Rings

Cleavage of Carbon–Carbon σ-Bonds of Four-Membered Rings

Tandem Nickel-Catalyzed Dimerization/(4+2) Cycloaddition of Terminal Alkynes with Four-Membered Ring Ketones

En Route to Furan-Fused Naphthopyrones: Formal Synthesis of the (+)-Lasionectrin and Its C12-Epimer

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