Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus

Wu, Deyan; Mei, Hanbing; Tan, Ping; Lü, Weiqiang; Zhu, Jin; Wang, Wei; Huang, Jin; Li, Jian

doi:10.1016/j.tetlet.2015.05.093

Cited by 23 publications

(17 citation statements)

References 35 publications

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“…The mp 97 °C is consistent with literature data. 62 1 H NMR (400 MHz, CDCl 3 ) δ: 7.80–7.51 (m, 2H), 7.23–6.99 (m, 2H), 4.65 (d, J = 15.6 Hz, 2H).…”

Section: Methodsmentioning

confidence: 99%

Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes

et al. 2020

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The following work presents three general approaches allowing, for the first time, the synthesis of 5,10-diheterotruxene derivatives containing two identical heteroatoms, namely, oxygen OOC , nitrogen NNC , or sulfur SSC . Two of described pathways involve the photocyclization of the corresponding triene 2 as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin 14 and benzo[ b ]heteroole 15 . Typical functionalizations of the 5,10-diheterotruxene core have also been presented. In addition, the article discusses the advantages and limitations of the three suggested paths for receiving specific 5,10-diheterotruxene derivatives because the universal method suitable for obtaining molecules with any type of heteroatoms is not known so far.

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“…The mp 97 °C is consistent with literature data. 62 1 H NMR (400 MHz, CDCl 3 ) δ: 7.80–7.51 (m, 2H), 7.23–6.99 (m, 2H), 4.65 (d, J = 15.6 Hz, 2H).…”

Section: Methodsmentioning

confidence: 99%

Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes

et al. 2020

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“…After the deprotection of 2l and 2aj,the tetraphenolic Alfafuran [21] (14)a nd triphenolic Wittifuran X [22] (15) were afforded in 86 %and 54 %yield, respectively.Coumestrol (16), aproliferate inhibitor of ovarian and breast cancer, [2] could be obtained in 11 %total yield from 2ab via asequence of formylation, Pinnick oxidation, demethylation, and automatic esterification. Moracin M [23] (17), aphosphodiesterase-4i nhibitor,w as also accessible from 2ac after simple transformation [24] in 88 %y ield. Through esterification with propargylic acid and palladium-catalyzed cyclization, [25] 2af could advance to anhydromarmesin (18)in39%yield.…”

Section: Angewandte Chemiementioning

confidence: 99%

Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran

et al. 2020

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An unprecedented deconstructive reorganization strategy for the de novo synthesis of hydroxylated benzofurans from kojic acid‐ or maltol‐derived alkynes is reported. In this reaction, both the benzene and furan rings were simultaneously constructed, whereas the pyrone moiety of the kojic acid or maltol was deconstructed and then reorganized into the benzene ring as a six‐carbon component. Through this strategy, at least one free hydroxyl group was introduced into the benzene ring in a substitution‐pattern tunable fashion without protection–deprotection and redox adjustment. With this method, a large number of hydroxylated benzofuran derivatives with different substitution‐patterns have been prepared efficiently. This methodology has also been shown as the key step in a collective total synthesis of hydroxylated benzofuran‐containing natural products (11 examples).

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“…Thek nown precursor 7ry was obtained in 56 %y ield from the dealkenylative alkenylation of the commercially available alkene 1r with the nitroolefin 4y;the synthesis of 7ry was achieved previously in 23 %yield in three steps staring from 3,5-dimethoxybromobenzene. [31] Finally,w eh ave achieved the synthesis of the drug (E)metanicotine (19), commonly known as rivanicline,d eveloped originally as ap otential treatment for Alzheimers disease. [32,33] Thedealkenylative alkenylation of the alkene 18 with the nitroolefin 4z proceeded smoothly to afford the intermediate 18 z,which, upon work-up and direct subjection to deprotection with 6 n HCl, afforded the drug 19 in an…”

Section: Angewandte Chemiementioning

confidence: 99%

Dealkenylative Alkenylation: Formal σ‐Bond Metathesis of Olefins

et al. 2020

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The dealkenylative alkenylation of alkene C(sp3)−C(sp2) bonds has been an unexplored area for C−C bond formation. Herein 64 examples of β‐alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β‐nitrostyrenes by ozone/FeII‐mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso‐moracin and the drug (E)‐metanicotine.

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Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus

Cited by 23 publications

References 35 publications

Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes

Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes

Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran

Dealkenylative Alkenylation: Formal σ‐Bond Metathesis of Olefins

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