6-Endo Heck Cyclization of 3-(2-Iodophenoxy)methylbenzofurans: A Useful Approach to Pterocarpenes

Fowler, Katherine J.; Ellis, Jillian L.; Morrow, Gary W.

doi:10.1080/00397911.2012.661910

Cited by 17 publications

(3 citation statements)

References 17 publications

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“…Strategically, the γ,δ-unsaturated ketone intermediate A , prone to isomerizing to the 2-(3-methylbenzofuran-2-yl)phenol driven by aromatization once upon formation, could be generated from the 3-(phenoxymethyl)benzofuran substrate B via a [3,3]-sigmatropic rearrangement . The precursor B can be facilely prepared from an etherification of benzofuran-3-ylmethanol C and phenol D by a Mitsunobu reaction …”

Section: Resultsmentioning

confidence: 99%

Collective Syntheses of 2-(3-Methylbenzofuran-2-yl)phenol-Derived Natural Products by a Cascade [3,3]-Sigmatropic Rearrangement/Aromatization Strategy

et al. 2017

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A cascade [3,3]-sigmatropic rearrangement/aromatization strategy to the synthesis of 2-(3-methylbenzofuran-2-yl)phenol derivatives was developed and applied to the collective syntheses of seven 2-arylbenzofuran-containing natural products, namely glycybenzofuran, glycyuralin E, lespedezol A, puerariafuran, 7,2',4'-trihydroxy-3-benzofurancarboxylic acid, coumestrol, and 4'-O-methylcoumestrol. Among them, the total syntheses of glycybenzofuran, glycyuralin E, puerariafuran, 7,2',4'-trihydroxy-3-benzofurancarboxylic acid, and 4'-O-methylcoumestrol were reported for the first time. The practicality of this novel strategy in preparation of the key intermediates was demonstrated by performing the reaction on gram scale and by synthesizing a series of natural products with 2-(3-methylbenzofuran-2-yl)phenol scaffolds in a common strategy.

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Section: Resultsmentioning

confidence: 99%

Collective Syntheses of 2-(3-Methylbenzofuran-2-yl)phenol-Derived Natural Products by a Cascade [3,3]-Sigmatropic Rearrangement/Aromatization Strategy

et al. 2017

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“…Compounds 3 -21 were identified by comparison of their spectroscopic data with those reported in the literature values as flemichapparin B (3), [10] [11] anhydrovariabilin (4), [12] 3,6a, 9-trimethoxypterocarpan (5), [13] (-)-variabilin (6), [14] (À)-phaseolin (7), [15] medicarpin (8), [16] (-)-maackiain (9), [6] phaseollidin (10), [17] biochanin A (11), [18] sophorophenolone (12), [19] 8-O-methylretusin (13), [20] afromosine (14), [21] formononetin (15), [22] cajanin (16), [22] and 4 0 ,7-dihydroxy-2 0 ,6-dimethoxyisoflavone (17). [23] The chemical property of the acetylated sub-fraction of this plant led to the isolation of isoflavone derivatives named 3-(benzo[d] [1,3]dioxol-5-yl)-4-oxo-4H-chromen-7-yl acetate (18), 7-acetoxy-4 0 -methoxyisoflavone (19), [24] 4 0 ,6 0 -diacetoxy-5-hydroxy-7-methoxyisoflavone (20), and 4 0 -acetoxy-5-hydroxy-7-methoxyisoflavone (21) which can be inferred back to the previously assigned structures named pseudobaptigenin, [25] formononetin (15), and cajanin (16), respectively (Fig.…”

Section: Resultsmentioning

confidence: 99%

Superbanone, A New 2‐Aryl‐3‐benzofuranone and Other Bioactive Constituents from the Tube Roots of Butea superba

Boonsombat

Prachyawarakorn

Pansanit

et al. 2017

Chemistry & Biodiversity

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Phytochemical investigation from the tube roots of Butea superba, led to the isolation and identification of a new 2-aryl-3-benzofuranone named superbanone (1), one benzoin, 2-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone (2), eight pterocarpans (3 - 10), and eleven isoflavonoids (11 - 21). Compound 2 was identified for the first time as a natural product. The structure of the isolated compounds was elucidated using spectroscopic methods, mainly 1D- and 2D-NMR. The isolated compounds and their derivatives were evaluated for α-glucosidase inhibitory and antimalarial activities. Compounds 3, 7, 8, and 11 showed promising α-glucosidase inhibitory activity (IC = 13.71 ± 0.54, 23.54 ± 0.75, 28.83 ± 1.02, and 12.35 ± 0.36 μm, respectively). Compounds 3 and 11 were twofold less active than the standard drug acarbose (IC = 6.54 ± 0.04 μm). None of the tested compounds was found to be active against Plasmodium falciparum strain 94. On the basis of biological activity results, structure-activity relationships are discussed.

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“…In past decades, many synthetic approaches have been developed to construct the basic fused tetracyclic structure. [1b], [1i], [1m], The FeCl 3 ‐mediated oxidative ring closure of 4‐hydroxy coumarins, which afforded coumestans in yields of 44–74 %, presents a classical synthetic strategy that focuses on the assembly of the furan nucleus of the chromenone scaffold , . Alternatively, the tandem construction of furan and pyranone rings by starting from 1,2‐bis(2‐alkoxyphenyl)ethynes or bis( o ‐methoxy)‐ cis ‐stilbene provides another route to coumestan and its analogues (32–77 % yield).…”

Section: Introductionmentioning

confidence: 99%

Tandem Demethylation/Annulation/Oxidation of 2,3‐Bis(2‐methoxyphenyl)‐3‐oxopropanals for One‐Pot Construction of Coumestans

et al. 2016

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A convenient and practical approach to coumestans has been successfully developed by using a one‐pot tandem demethylation/annulation/oxidation reaction sequence that employs easily accessible 2,3‐bis(2‐methoxyphenyl)‐3‐oxopropanals as the starting material. This synthetic protocol provided a variety of coumestan derivatives in good to excellent yields under mild conditions. The exploration of biologically active coumestan compounds is a potential application of this synthetic method.

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6-Endo Heck Cyclization of 3-(2-Iodophenoxy)methylbenzofurans: A Useful Approach to Pterocarpenes

Cited by 17 publications

References 17 publications

Collective Syntheses of 2-(3-Methylbenzofuran-2-yl)phenol-Derived Natural Products by a Cascade [3,3]-Sigmatropic Rearrangement/Aromatization Strategy

Collective Syntheses of 2-(3-Methylbenzofuran-2-yl)phenol-Derived Natural Products by a Cascade [3,3]-Sigmatropic Rearrangement/Aromatization Strategy

Superbanone, A New 2‐Aryl‐3‐benzofuranone and Other Bioactive Constituents from the Tube Roots of Butea superba

Tandem Demethylation/Annulation/Oxidation of 2,3‐Bis(2‐methoxyphenyl)‐3‐oxopropanals for One‐Pot Construction of Coumestans

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