The First Synthesis of Natural Occurring Juncaceae Coumarin, 9‐Hydroxy‐8‐methyl‐3<i>H</i>‐benzo[<i>f</i>]chromen‐3‐one, Featuring a One‐pot Rearrangement and Aromatization Cascade

Hon, Yung‐Son; Hong, Ya-Chun; Hong, Bor‐Cherng; Liao, Ju‐Hsiou

doi:10.1002/jccs.201100481

Cited by 3 publications

(3 citation statements)

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“…From the Juncus acutus plant's rhizomes, Della-Greca and colleagues extracted several bioactive benzocoumarins which symbolized as BC 31-BC37 [31]. Then, starting with β-tetralone and through two different pathways including a onepot aromatization and rearrangement chain reactions, Hon's research team reported the total synthesis of the BC33 for the first time [74].…”

Section: Juncus Benzocoumarin Total Synthesismentioning

confidence: 99%

Untitled

2022

J. Med. Chem. Sci.

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Section: Juncus Benzocoumarin Total Synthesismentioning

confidence: 99%

Untitled

2022

J. Med. Chem. Sci.

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“…[4][5] Recent years have witnessed increasing interest in π-expanded coumarins, as they display a wide spectrum of biological activities (Figure 1). [6] Therefore, the ability to quickly assemble a πexpanded coumarin from a readily available starting material is highly significant. [7] 5,6-Benzocoumarin is an important π-expanded coumarin motif, with various routes for its synthesis having been reported (Scheme 1).…”

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confidence: 99%

“…Examples of synthetic biologically active π-expanded coumarins. [6] Scheme 1. Synthetic routes to 5,6-benzocoumarins.…”

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Synthesis of π‐Expanded Coumarins by Ligand‐Enabled Selective C−H Functionalization

Ren

Xing

et al. 2022

Adv Synth Catal

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Herein, we report the synthesis of a series of π‐expanded coumarin derivatives by the selective C−H alkenylation of β‐naphthol in the presence of a palladium catalyst. The use of an anionic thioether ligand is critical for ensuring the high reactivity of this reaction; it enables low catalyst loadings, mild reaction conditions, and the use of acetic acid as a green solvent. This chemistry is widely applicable to naphthol‐based aromatic substrates bearing either electron‐donating or ‐withdrawing functional groups.

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Total syntheses of (–)-macrocalyxoformins A and B and (–)-ludongnin C

Cao,

Sun,

Zhang

et al. 2024

Nat Commun

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The complex and diverse molecular architectures along with broad biological activities of ent-kauranoids natural products make them an excellent testing ground for the invention of synthetic methods and strategies. Recent efforts notwithstanding, synthetic access to the highly oxidized enmein-type ent-kauranoids still presents considerable challenges to synthetic chemists. Here, we report the enantioselective total syntheses of C-19 oxygenated enmein-type ent-kauranoids, including (–)-macrocalyxoformins A and B and (–)-ludongnin C, along with discussion and study of synthetic strategies. The enabling feature in our synthesis is a devised Ni-catalyzed decarboxylative cyclization/radical-polar crossover/C-acylation cascade that forges a THF ring concomitantly with the β-keto ester group. Mechanistic studies reveal that the C-acylation process in this cascade reaction is achieved through a carboxylation followed by an in situ esterification. Biological evaluation of these synthetic natural products reveals the indispensable role of the ketone on the D ring in their anti-tumor efficacy.

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The First Synthesis of Natural Occurring Juncaceae Coumarin, 9‐Hydroxy‐8‐methyl‐3H‐benzo[f]chromen‐3‐one, Featuring a One‐pot Rearrangement and Aromatization Cascade

Abstract: The synthesis of benzocoumarins from b-tetralones has been achieved via two pathways in the first total synthesis of the Juncaceae natural product, 9-hydroxy-8-methyl-3H-benzo[f]chromen-3-one, featuring a one-pot rearrangement and aromatization cascade.

Cited by 3 publications

References 48 publications

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Untitled

Synthesis of π‐Expanded Coumarins by Ligand‐Enabled Selective C−H Functionalization

Total syntheses of (–)-macrocalyxoformins A and B and (–)-ludongnin C

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