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Synthesis and Applications of Hajos-Parrish Ketone Isomers.

ABSTRACT: Numerous natural products possess ring systems and functionality for which Hajos-Parrish ketone isomers with a transposed methyl group (termed "iso-Hajos-Parrish ketones") would be of value. However, such building blocks have not been exploited to the same degree as the more typical Hajos-Parrish hydrindane. An efficient three-step synthesis of such materials was fueled by a simple method for the rapid preparation of highly functionalized cyclopentenones, several of which are new chemical entities that would be challenging to access through other approaches. Furthermore, one iso-Hajos-Parrish ketone was converted into two distinct natural product analogues and one natural product. As one indication of the value of these new building blocks, that latter target was obtained in 10?steps, having previously been accessed in 18?steps using the Hajos-Parrish ketone.

SUBMITTER: Eagan JM

PROVIDER: S-EPMC4737474 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Synthesis and Applications of Hajos-Parrish Ketone Isomers.

Eagan James M JM Hori Masahiro M Wu Jianbin J Kanyiva Kyalo Stephen KS Snyder Scott A SA

Angewandte Chemie (International ed. in English) 20150514 27

Numerous natural products possess ring systems and functionality for which Hajos-Parrish ketone isomers with a transposed methyl group (termed "iso-Hajos-Parrish ketones") would be of value. However, such building blocks have not been exploited to the same degree as the more typical Hajos-Parrish hydrindane. An efficient three-step synthesis of such materials was fueled by a simple method for the rapid preparation of highly functionalized cyclopentenones, several of which are new chemical entiti ...[more]

PMID: 25974879

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Project description:Polyether ether ketone is a bioinert polymer, that is of high interest in research and medicine as an alternative material for the replacement of bone implants made of metal. The biggest deficit of this polymer is its hydrophobic surface, which is rather unfavorable for cell adhesion and thus leads to slow osseointegration. In order to address this drawback, 3D-printed and polymer extruded polyether ether ketone disc samples that were surface-modified with titanium thin films of four different thicknesses via arc evaporation were investigated and compared with non-modified disc samples. Depending on the modification time, the thickness of the coatings ranged from 40 nm to 450 nm. The 3D-printing process does not affect the surface or bulk properties of polyether ether ketone. It turned out that the chemical composition of the coatings obtained did not depend on the type of substrate. Titanium coatings contain titanium oxide and have an amorphous structure. Microdroplets formed on the sample surfaces during treatment with an arc evaporator contain a rutile phase in their composition. Surface modification of the samples via arc evaporation resulted in an increase in the arithmetic mean roughness from 20 nm to 40 nm for the extruded samples and from 40 nm to 100 nm for the 3D-printed samples, with the mean height difference increasing from 100 nm to 250 nm and from 140 nm to 450 nm. Despite the fact that the hardness and reduced elastic modulus of the unmodified 3D-printed samples (0.33 GPa and 5.80 GPa) are higher than those of the unmodified extruded samples (0.22 GPa and 3.40 GPa), the surface properties of the samples after modification are approximately the same. The water contact angles of the polyether ether ketone sample surfaces decrease from 70° to 10° for the extruded samples and from 80° to 6° for the 3D-printed samples as the thickness of the titanium coating increases, making this type of coating promising for biomedical applications.

Dataset Information

Synthesis and Applications of Hajos-Parrish Ketone Isomers.

Publications

Synthesis and Applications of Hajos-Parrish Ketone Isomers.

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