Reaction of dimethyl sodio-3-ketoglutarate with glyoxal and substituted glyoxals: First expeditious preparation of bicyclo[3.3.0]octane-3,7-dione; synthesis and crystal structure of 5,7-dihydroxy-4-methoxycarbonyl-3-phenyl-1-indanone

doi:10.1016/0040-4020(82)85046-1

Paper

Reaction of dimethyl sodio-3-ketoglutarate with glyoxal and substituted glyoxals: First expeditious preparation of bicyclo[3.3.0]octane-3,7-dione; synthesis and crystal structure of 5,7-dihydroxy-4-methoxycarbonyl-3-phenyl-1-indanone

Published 1982 · S. Bertz, G. Rihs, R. Woodward

Tetrahedron

Q3 SJR score

29

Citations

2

Influential Citations

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Abstract

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Study Snapshot

This study presents a simple two-step preparation of bicyclo[3.3.0]octane-3,7-dione using dimethyl 3-ketoglutarate and glyoxal, with a novel hydrogen bonding phenomenon revealed in the crystal structure of indanone.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Reaction of dimethyl sodio-3-ketoglutarate with glyoxal and substituted glyoxals: First expeditious preparation of bicyclo[3.3.0]octane-3,7-dione; synthesis and crystal structure of 5,7-dihydroxy-4-methoxycarbonyl-3-phenyl-1-indanone

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References

Crystal and molecular structure of a pentagonal dodecahedrane.

The 1,16-dimethyl derivative of pentagonal dodecahedrane has D(3d) symmetry and unusual physical properties, with only small distortions from pure dodecahedral symmetry due to alkyl groups.

Correlations between proton chemical shift tensors, deuterium quadrupole couplings, and bond distances for hydrogen bonds in solids

The isotropic value of chemical shift tensors correlates well with both ROO and e2qQ/h, while anisotropy shows more scatter.

Citations

A synthetic approach to 5/5/6-polycyclic tetramate macrolactams of the discodermide type

This study developed a flexible synthetic route to polycyclic tetramate macrolactams, offering a short approach to various stereoisomers of the 5/5/6-tricarbocyclic motif found in discodermide and other PTMs.

Substituent and intramolecular hydrogen-bond effect on the fluorescent emission of two easy-synthesizable fused rigid bicyclic octadiene derivatives

The fluorescence emission of fused rigid bicyclic octadiene derivatives is mainly quenched by an intramolecular hydrogen bond, likely due to molecular rigidity.

Di-tert-butyl N,N′-(octahydropentalene-2,5-diyl)dicarbamate

This novel self-assembling molecule demonstrates a constrained bicyclo[3.3.0]octane template, which can be used to design novel self-assembling motifs with potential applications in biomedicine.

A rigid bicyclo[3.3.0]octane (octahydropentalene): a heavily constrained novel aliphatic template for molecular self-assembly

The rigid bicyclo[3.3.0]octane aliphatic template allows for conformationally ordered molecular self-assembly, offering potential for self-assembling systems with conformationally ordered features.

Five bicyclo[3.3.0]octa-2,6-dienes.

The five compounds studied show a butterfly-like conformation and strong intramolecular hydrogen bonds between -OH and C=O groups.

Condensation of Dimethyl 1,3-Acetonedicarboxylate with 1,2-Dicarbonyl Compounds: cis-bicyclo[3.3.0]octane-3,7-diones

Condensation of Dimethyl 1,3-Acetonedicarboxylate with 1,2-Dicarbonyl produces cis-Bicyclo[3.3.0]octane-3,7-diones, which can be converted into cis-1,5-Dimethylbic

Lipase-catalyzed asymmetric demethoxycarbonylation: Formal syntheses of (+)-carbacyclin, (−)-ajmalicine, and (−)-tetrahydroalstonine

Lipase-catalyzed asymmetric demethoxycarbonylation allows for the enantiomerically pure preparation of (+)-carbacyclin, ()-ajmalicine, and ()-tetrahydroalstonine.