Divergent and concise total syntheses of dihydrochalcones and 5-deoxyflavones recently isolated from Tacca species and Mimosa diplotricha

Sum, Tze Han; Stokes, Jamie E.; Galloway, Warren R. J. D.; Spring, David R.

doi:10.1016/j.tet.2015.02.017

Cited by 22 publications

(13 citation statements)

References 42 publications

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“…Accordingly, the first synthetic application was started with the synthesis of taccabulin C employing salicylaldehyde 1i and vinyl ketone 2h under Rh‐catalyzed conditions (Scheme ). Our method thus proved to be very useful as the desired coupling underwent smoothly without protection of the phenolic group in salicylaldehyde 1i and vinyl ketone 2h . This directly afforded taccabulin C ( 5b ) in 62 % yield.…”

Section: Resultsmentioning

confidence: 89%

“…Taccabulins can be synthesized from the corresponding o ‐hydroxychalcones (Scheme a) . This approach in general, is problematic as the preparation of o ‐hydroxychalcones involves tedius synthetic procedures often with low yields due to the presence of free phenolic group.…”

Section: Introductionmentioning

confidence: 99%

“…This approach in general, is problematic as the preparation of o ‐hydroxychalcones involves tedius synthetic procedures often with low yields due to the presence of free phenolic group. [3a] Further, synthesis of o ‐hydroxydihydrochalcones with direct use of salicylaldehydes was also reported with protection/deprotection synthetic manoeuvring to obtain improved yields …”

Section: Introductionmentioning

confidence: 99%

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Rh‐Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A–E

Rao

Ramakrishna

2019

Eur J Org Chem

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Section: Resultsmentioning

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Rh‐Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A–E

Rao

Ramakrishna

2019

Eur J Org Chem

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“…The total synthesis of several naturally occurring dihydrochalcones (taccabulins B-E and evelynin) and 5-deoxyflavones, using Algar-Flynn-Oyamada oxidation and benzoquinone C-H activation, has been described by Sum et al [59]. Dihydrochalcones can be also obtained from commercially available flavones, like quercetin or naringenin, in a five-step process with moderate yield (from 23% to 37%) [60].…”

Section: Chemical Synthesis Of Dihydrochalconesmentioning

confidence: 99%

Dihydrochalcones: Methods of Acquisition and Pharmacological Properties—A First Systematic Review

2019

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Dihydrochalcones are a class of secondary metabolites, for which demand in biological and pharmacological applications is still growing. They posses several health-endorsing properties and, therefore, are promising candidates for further research and development. However, low content of dihydrochalcones in plants along with their low solubility and bioavailability restrict the development of these compounds as clinical therapeutics. Therefore, chemomicrobial and enzymatic modifications are required to expand their application. This review aims at analyzing and summarizing the methods of obtaining dihydrochalcones and of presenting their pharmacological actions that have been described in the literature to support potential future development of this group of compounds as novel therapeutic drugs. We have also performed an evaluation of the available literature on beneficial effects of dihydrochalcones with potent antioxidant activity and multifactorial pharmacological effects, including antidiabetic, antitumor, lipometabolism regulating, antioxidant, anti-inflammatory, antibacterial, antiviral, and immunomodulatory ones. In addition, we provide useful information on their properties, sources, and usefulness in medicinal chemistry.

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“…Flavonoids are a large family of polyphenolic compounds that represent dietary constituents of importance to good health as well as a potentially important new class of pharmaceutical lead substrates [1,2,3]. There are several subclasses of flavonoids, including aurones, chalcones, coumarins, flavones and isoflavones, which serve as the core structural units of numerous biologically active molecules [4,5,6,7].…”

Section: Introductionmentioning

confidence: 99%

Combinatorial Synthesis of Structurally Diverse Triazole-Bridged Flavonoid Dimers and Trimers

et al. 2016

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Flavonoids are a large family of compounds associated with a broad range of biologically useful properties. In recent years, synthetic compounds that contain two flavonoid units linked together have attracted attention in drug discovery and development projects. Numerous flavonoid dimer systems, incorporating a range of monomers attached via different linkers, have been reported to exhibit interesting bioactivities. From a medicinal chemistry perspective, the 1,2,3-triazole ring system has been identified as a particularly attractive linker moiety in dimeric derivatives (owing to several favourable attributes including proven biological relevance and metabolic stability) and triazole-bridged flavonoid dimers possessing anticancer and antimalarial activities have recently been reported. However, there are relatively few examples of libraries of triazole-bridged flavonoid dimers and the diversity of flavonoid subunits present within these is typically limited. Thus, this compound type arguably remains underexplored within drug discovery. Herein, we report a modular strategy for the synthesis of novel and biologically interesting triazole-bridged flavonoid heterodimers and also very rare heterotrimers from readily available starting materials. Application of this strategy has enabled step-efficient and systematic access to a library of structurally diverse compounds of this sort, with a variety of monomer units belonging to six different structural subclasses of flavonoid successfully incorporated.

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Divergent and concise total syntheses of dihydrochalcones and 5-deoxyflavones recently isolated from Tacca species and Mimosa diplotricha

Cited by 22 publications

References 42 publications

Rh‐Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A–E

Rh‐Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A–E

Dihydrochalcones: Methods of Acquisition and Pharmacological Properties—A First Systematic Review

Combinatorial Synthesis of Structurally Diverse Triazole-Bridged Flavonoid Dimers and Trimers

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