A vicarious, one-pot synthesis of benzo- and naphthofurans: Applications to the syntheses of stereumene B and paeoveitols

Rashid, Showkat; Bhat, Bilal A.; Mehta, Goverdhan

doi:10.1016/j.tetlet.2019.03.037

Cited by 17 publications

(11 citation statements)

References 37 publications

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“…Naphthofurans fused or coupled with oxygen and nitrogen heterocycles do not occur in nature. Even synthetic naphthofurans coupled or fused with oxygen and nitrogen heterocycle are not reported so far, except for some reports of such compounds from this literature method [73][74][75][76][77][78]. These observations prompted us to undertake the investigation of naphthofuran with oxadiazole and indole as second heterocyclic components.…”

Section: Biologically Active Naphthofuransmentioning

confidence: 99%

Synthesis, reactions and applications of naphthofurans: A review

Abdelwahab

Fekry

2021

Eur J Chem

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Considering the highly important biological and medicinal properties of naphthofurans, the synthesis of these heterocycles has attracted the interest of medicinal and organic chemists. This review aims to describe the different strategies developed so far for the synthesis of naphthofurans and their applications and the literature reports for the period of 2000 to early 2020. After a brief introduction of the types of naphthofurans and their biological activities, the different synthetic approaches such as chemical and photochemical, methods are described and organized on the basis of the catalysts and the other reagents employed in the syntheses. Some of the reactions have been applied successfully to the synthesis of biologically important compounds.

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Section: Biologically Active Naphthofuransmentioning

confidence: 99%

Synthesis, reactions and applications of naphthofurans: A review

Abdelwahab

Fekry

2021

Eur J Chem

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“…Recently, Mehta and co-workers, during an attempt to perform a Tanabe annulation [193] on 4-hydroxy-cyclohexanone with 1,1-dimethoxy acetone, obtained the corresponding 3-methybenzofuran as the only product in 78% yield [194] (Scheme 62). This method was extended to naphthofurans and other related frameworks.…”

Section: Benzoannulationmentioning

confidence: 99%

Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans

Chiummiento¹,

D’Orsi²,

Funicello³

et al. 2020

Molecules

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This review describes the progress of the last decade on the synthesis of substituted benzofurans, which are useful scaffolds for the synthesis of numerous natural products and pharmaceuticals. In particular, new intramolecular and intermolecular C–C and/or C–O bond-forming processes, with transition-metal catalysis or metal-free are summarized. (1) Introduction. (2) Ring generation via intramolecular cyclization. (2.1) C7a–O bond formation: (route a). (2.2) O–C2 bond formation: (route b). (2.3) C2–C3 bond formation: (route c). (2.4) C3–C3a bond formation: (route d). (3) Ring generation via intermolecular cyclization. (3.1) C7a-O and C3–C3a bond formation (route a + d). (3.2) O–C2 and C2–C3 bond formation: (route b + c). (3.3) O–C2 and C3–C3a bond formation: (route b + d). (4) Benzannulation. (5) Conclusion.

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“…Stereumene B (95) showed weak nematocidal activity against C. elegans with a fatality rate of 41.1% at 200 μg mL −1 in 24 h [ 54 ]. Showkat et al found that stereumene B (95) could be synthesized via a TiCl 4 -mediated Tanabe protocol by employing a series of functionalized benzo- and naphthofurans from cyclohexanone precursors [ 55 ].…”

Section: Secondary Metabolites From Stereum Andmentioning

confidence: 99%

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

Tian

Zhao

et al. 2020

Microorganisms

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Natural metabolites from microorganisms play significant roles in the discovery of drugs, both for disease treatments in humans, and applications in agriculture. The Basidiomycetes Stereum genus has been a source of such bioactive compounds. Here we report on the structures and activities of secondary metabolites from Stereum. Their structural types include sesquiterpenoids, polyketides, vibralactones, triterpenoids, sterols, carboxylic acids and saccharides. Most of them showed biological activities including cytotoxic, antibacterial, antifungal, antiviral, radical scavenging activity, autophagy inducing activity, inhibiting pancreatic lipase against malarial parasite, nematocidal and so on. The syntheses of some metabolites have been studied. In this review, 238 secondary metabolites from 10 known species and various unidentified species of Stereum were summarized over the last seven decades.

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A vicarious, one-pot synthesis of benzo- and naphthofurans: Applications to the syntheses of stereumene B and paeoveitols

Cited by 17 publications

References 37 publications

Synthesis, reactions and applications of naphthofurans: A review

Synthesis, reactions and applications of naphthofurans: A review

Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

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