Total Syntheses of Balsacone B and Balsacone C

Burmaoğlu, Serdar

doi:10.18596/jotcsa.311736

Cited by 3 publications

(4 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The direct cinnamylation of dihydrochalcones is a plausible biosynthetic route to balsacones . Nevertheless, the construction of a dihydrochalcone scaffold from petrochemicals would likely rely on tedious synthetic sequences including protection steps, differentiation of phenol functions, and a Friedel–Crafts acylation using harmful reagents . On the other hand, several dihydrochalcones 2 are abundant in various plant extracts , or readily accessible by the microbial or catalytic transformation of naturally occurring flavanones .…”

Section: Introductionmentioning

confidence: 99%

Exploring the Biomass-Derived Chemical Space Emerging from Natural Dihydrochalcones through the Single-Step Hemisynthesis of Antibacterial Balsacones

Alsarraf

Bilodeau

Legault

et al. 2020

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

The preparation of bioactive molecules from biomass substrates is a relevant approach to replace fossil resources. The substitution patterns of natural products facilitate the access to polyfunctional molecules; yet, only few families of biosourced compounds have been valued in this way. Renewable dihydrochalcones and cinnamyl alcohols were combined in an expedient hemisynthesis of balsacones A, B, and C. These potent antibacterial compounds were prepared following a single-step Brønsted acidcatalyzed metal-free and protective-group-free Friedel−Crafts alkylation protocol. Novel analogues were also readily accessible relying on the diversity of biosourced precursors.

show abstract

Section: Introductionmentioning

confidence: 99%

Exploring the Biomass-Derived Chemical Space Emerging from Natural Dihydrochalcones through the Single-Step Hemisynthesis of Antibacterial Balsacones

Alsarraf

Bilodeau

Legault

et al. 2020

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…The hemi-syntheses of dihydrochalcone analogues, known as balsacones, were reported to have been performed using their precursors, which are also dihydrochalcones [ 14 , 15 ]. Populus balsamifera (Salicaceae) grows in different regions of North America, and its buds have been traditionally used to treat wounds.…”

Section: Introductionmentioning

confidence: 99%

“…Phenolic dihydrochalcones and cinnamyl alcohols were combined in the hemi-syntheses of balsacones A, B, and C ( Figure 2 ) from bio-sourced dihydrochalcone, and these compounds were produced through a single-step process involving acid-catalysed Friedel–Crafts alkylation reaction [ 15 ]. Total synthesis of balsacones B and C using a synthetic method is also known [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Asebogenin and Balsacone A Precursor by a Novel Synthetic Strategy: Recent Opportunities for and Challenges of Total Synthesis of Balsacone A

Polat

2022

Molecules

View full text Add to dashboard Cite

One of the main areas of interest of synthetic organic chemistry is the rapid construction of small molecules with proven diverse biological activities for the development of new strategies to cure human health. In particular, the development of novel synthetic strategies is the most important option for reaching the molecular scaffolds of active molecules of natural origin. Balsacone A and asebogenin are compounds that exhibit a wide variety of important biological activities. In this respect, it has become very important to develop new strategies for the construction of biologically active natural and synthetic balsacone analogues. In particular, balsacone derivatives with hydroxy-substituted dihydrochalcone skeletons can be isolated from plant sources or obtained by hemi-syntheses using bio-sourced precursors. An efficient synthetic strategy to synthetically obtain balsacone A is the aim of the present study that considers the limited natural availability of these molecules as well as other factors, such as cost and time. Starting with phloroglucinol, a nine-step synthesis of the precursor of balsacone A was achieved at a 10% overall yield. Furthermore, asebogenin, which has a dihydrochalcone structure and plays a key role in the synthesis of balsacone A, was synthesised with a good yield.

show abstract

“…Little is known about Balsacone C's effects on S. aureus and E. coli. Balsacone C may help treat methicillin-resistant S. aureus (MRSA) infections and most likely works by altering the structure of bacterial cell membranes (6). Currently, research surrounding Balsacone C and the pathogens it may treat is limited.…”

Section: Introductionmentioning

confidence: 99%

The analysis of the antimicrobial benefits of Populus balsamifera

Breen,

Onufrock

2021

J Emerg Invest

View full text Add to dashboard Cite

This study was conducted to explore a new potential treatment for bacterial infections. This study aimed to investigate the antimicrobial properties of the tree species, Populus balsamifera. The objective was to determine the effectiveness of extract from the buds of P. balsamifera in inhibiting bacterial growth. A Kirby-Bauer assay was used to assess the efficacy of P. balsamifera extract against gram-negative and gram-positive bacterial growth. It was observed that the extract of the buds of P. balsamifera was highly effective against gram-positive bacteria. This helps to indicate the potential use of P. balsamifera in the medical field to eliminate gram-positive bacteria.

show abstract

Total Syntheses of Balsacone B and Balsacone C

Cited by 3 publications

References 24 publications

Exploring the Biomass-Derived Chemical Space Emerging from Natural Dihydrochalcones through the Single-Step Hemisynthesis of Antibacterial Balsacones

Exploring the Biomass-Derived Chemical Space Emerging from Natural Dihydrochalcones through the Single-Step Hemisynthesis of Antibacterial Balsacones

Synthesis of Asebogenin and Balsacone A Precursor by a Novel Synthetic Strategy: Recent Opportunities for and Challenges of Total Synthesis of Balsacone A

The analysis of the antimicrobial benefits of Populus balsamifera

Contact Info

Product

Resources

About