Abstract:Functionalized hydropentalenes (i.e., bicyclo[3.3.0]octanones) constitute important building blocks for natural products and for ligands for asymmetric catalysis. The assembly and tailored functionalization of this convex roof-shaped scaffold is challenging and has motivated a variety of synthetic approaches including our own contributions, which will be presented in this account.1 Introduction2 Biosynthesis of Hydropentalenes3 Hydropentalenes through the Pauson–Khand Reaction4 Hydropentalenes through Tran… Show more
“…After that, the catalyst was filtered off, the filtrate was concentrated in vacuo, and the residue was used in further transformations with no additional treatment. 1 H NMR of the material obtained was not characteristic due to the partial deprotection of ketone and complexity of the spectrum. The yield was calculated as quantitive, ~5.1 g.…”
“…The quest to harness the potential of tetrahydropentalene (THP) derivatives in medicinal chemistry is driven by the remarkable biological activities observed for natural products featuring the bicyclo [3.3.0]octane core, such as carbacyclin (1,Figure), and clinprost (3). These compounds show prostaglandin analogs and platelet aggregation inhibitory properties, along with others displaying the anticancer activity like cylindramide (2), and antibiotic potential like geodin A (4).…”
Section: ■ Introductionmentioning
confidence: 99%
“…These compounds show prostaglandin analogs and platelet aggregation inhibitory properties, along with others displaying the anticancer activity like cylindramide (2), and antibiotic potential like geodin A (4). In general, they exemplify the diverse biological actions -from antimicrobial to enzyme-inhibiting activities -that THP structural motif offers [1]. The synthetic analogs of tetrahydropentalenes, thus, emerge as formidable scaffolds in the drug development, opening the opportunities for finding new therapeutic agents capable of targeting a broad spectrum of diseases.…”
Section: ■ Introductionmentioning
confidence: 99%
“…An in-depth review of the methodologies used for synthesizing tetrahydropentalene derivatives reveals a dynamic landscape marked by both tradition and novelty [1]. Each strategy offers unique advantages, such as enhanced yields and selectivity, yet often contends with the need for specialized reagents and stringent conditions, reflecting the evolving sophistication in the tetrahydropentalene synthesis.…”
Inspired by the bioactivity of natural compounds with a bicyclo[3.3.0]octane core, the study focuses on developing tetrahydropentalene-2,5-dione (2,5-THP-dione) derivatives as potential building blocks for the use in medicinal chemistry. Using the commercially available 2,5-THP-dione, a number of alkylated derivatives and a monofunctional ketone were synthesized. Using optimized protocols for synthesis, target compounds were obtained with high yields on a multigram scale. These compounds are promising derivatives for further chemical derivatization and therapeutic use, and thus highlight the value of 2,5-THP-dione in creating complex molecular structures for drug discovery, as well as the importance of tetrahydropentalene derivatives as valuable building blocks in synthetic chemistry.
“…After that, the catalyst was filtered off, the filtrate was concentrated in vacuo, and the residue was used in further transformations with no additional treatment. 1 H NMR of the material obtained was not characteristic due to the partial deprotection of ketone and complexity of the spectrum. The yield was calculated as quantitive, ~5.1 g.…”
“…The quest to harness the potential of tetrahydropentalene (THP) derivatives in medicinal chemistry is driven by the remarkable biological activities observed for natural products featuring the bicyclo [3.3.0]octane core, such as carbacyclin (1,Figure), and clinprost (3). These compounds show prostaglandin analogs and platelet aggregation inhibitory properties, along with others displaying the anticancer activity like cylindramide (2), and antibiotic potential like geodin A (4).…”
Section: ■ Introductionmentioning
confidence: 99%
“…These compounds show prostaglandin analogs and platelet aggregation inhibitory properties, along with others displaying the anticancer activity like cylindramide (2), and antibiotic potential like geodin A (4). In general, they exemplify the diverse biological actions -from antimicrobial to enzyme-inhibiting activities -that THP structural motif offers [1]. The synthetic analogs of tetrahydropentalenes, thus, emerge as formidable scaffolds in the drug development, opening the opportunities for finding new therapeutic agents capable of targeting a broad spectrum of diseases.…”
Section: ■ Introductionmentioning
confidence: 99%
“…An in-depth review of the methodologies used for synthesizing tetrahydropentalene derivatives reveals a dynamic landscape marked by both tradition and novelty [1]. Each strategy offers unique advantages, such as enhanced yields and selectivity, yet often contends with the need for specialized reagents and stringent conditions, reflecting the evolving sophistication in the tetrahydropentalene synthesis.…”
Inspired by the bioactivity of natural compounds with a bicyclo[3.3.0]octane core, the study focuses on developing tetrahydropentalene-2,5-dione (2,5-THP-dione) derivatives as potential building blocks for the use in medicinal chemistry. Using the commercially available 2,5-THP-dione, a number of alkylated derivatives and a monofunctional ketone were synthesized. Using optimized protocols for synthesis, target compounds were obtained with high yields on a multigram scale. These compounds are promising derivatives for further chemical derivatization and therapeutic use, and thus highlight the value of 2,5-THP-dione in creating complex molecular structures for drug discovery, as well as the importance of tetrahydropentalene derivatives as valuable building blocks in synthetic chemistry.
Fischer indole reaction of Weiss diketone with 4‐bromophenylhydrazine provided the 2,8‐dibromo‐hexahydropentaleno[2,1‐b:5,4‐b’]diindole key intermediate, which was converted to the target compounds by N‐protection/Suzuki cross‐coupling. Variation of protecting groups, mesogenic units, and their alkoxy substitution gave calamitic diindole mesogens. Both N‐protection and alkoxy chain influenced the mesomorphic properties of phenyl diindoles. Among the differently N‐protected derivatives only ethylcarbamate‐protected ones formed enantiotropic mesophases. Mesophase range and type were controlled by the chain lengths: chains≤C12 gave nematic (N) phases, diindoles with side chains≥C14 formed additional lower temperature smectic (SmA) phases. Irrespective of the chain lengths 4′‐alkyloxybiphenyl diindoles formed N and SmA phases upon first heating but tended to decomposition below their clearing points. X‐ray crystal structure analysis of bis(4′‐decyloxy)biphenyl diindole reveals that in the solid‐state the folding angle of the hydropentalene core caused an almost perpendicular orientation of the two indole/biphenyl parts with respect to each other.
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