Synthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8 hexols (Bishomoinositols) as glycosidase inhibitors

Date

2008-06-20

Author

Baran, Arif
Guenel, Aslihan
Balcı, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

176
views

0
downloads

For the construction of the bicyclo[2.2.2] octane skeleton, 2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole was reacted with vinylene carbonate to give two isomeric cycloadditon products having the bicyclo[2.2.2]octane skeleton. Hydrolysis of the ketal ring and the opening of the carbonate functionality, followed by hydroxylation of the remaining double bond resulted in the formation of a symmetrical hexol. Epoxidation of the double bond in the cycloaddition products and the subsequent ring-opening reactions produce two additional hexol derivatives. One of the synthesized molecules exhibited enzyme-specific inhibition against alpha-glycosidase.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/57615

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo800553u

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Synthesis of Ferrocenyl Substituted Aziridines Zeytinci, Serhat; Doğan, Özdemir; Department of Chemistry (2006) Immobilization of tyrosinase enzyme was performed in the matrices obtained via copolymerization of terephthalic acid bis-(2-thiophen-3-yl ethyl) ester (TATE) with pyrrole. During electrochemical polymerization of pyrrole, enzyme molecules were entrapped in the copolymer matrice. Activity measurements were performed by using Besthorn̕s Hydrazone method which includes spectrophotometric analysis of quinones produced by the enzyme. Enzyme electrodes were characterized in terms of maximum reaction rate (Vmax) a...
Addition of trifluoromethyltrimethylsilane to acyl phosphonates: Synthesis of TMS-Protected 1-alkyl-1-trifluoromethyl-1-hydroxyphosphonates and 1-aryldifluoroethenyl phosphates Demir, Ayhan Sıtkı; Eymur, Serkan (American Chemical Society (ACS), 2007-10-26) Addition reactions of nucleophilic CF3TMS to acyl phosphonates were investigated. Various acyl phosphonates reacted readily with CF3TMS in the presence of K2CO3 in DMF at rt to give 1-alkyl-2,2,2-trifluoro-1-trimethylsilyloxyethylphosphonate in 70−90% yields. When benzoyl phosphonates were used as starting material, after addition of CF3, the formed alcoholate undergoes phosphonate−phosphate rearrangement to form the acyl anion, followed by elimination of F- to give 1-aryldifluoroethenyl phosphates in 87−97...
Synthesis of ferrocenyl quinones and polyquinanes Eralp, Tuğçe; Zora, Metin; Department of Chemistry (2005) With the discovery of antitumor activity of ferrocene derivatives, research on new ferrocene derivatives have gained importance. For this purpose, we have investigated the synthesis of ferrocenyl quinones starting from squaric acid. Several quinone derivatives are known to have antitumor and antibiotic activities. In this research, by combining ferrocene and quinone moieties, we have targeted ferrocenyl quinones which are supposed to have enhanced potential antitumor activity. Thermolysis of ferrocenyl-subs...
Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005) A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
Synthesis and structure of cyclopropano-annelated homosesquinorbornene derivatives containing pyramidalized double bonds: Evidence for the sterical effect of a cyclopropyl. group on the degree of C=C double-bond pyramidalization Saracoglu, N; Talaz, O; Azizoglu, A; Watson, WH; Balcı, Metin (American Chemical Society (ACS), 2005-07-08) endo- and exo-2,3,4,7-tetrahydro-1H-1,4-methanobenzoeyeloheptene-7-carboxylic acid ethyl esters have been synthesized, and their Diels-Alder cycloaddition reactions with maleic anhydride, dimethyl acetylenedicarboxylate and singlet oxygen have been investigated. The X-ray analysis of four adducts indicated the pyramidalization of the central double bond. Density functional theory calculations on the isolated products and model compounds showed excellent agreement between the experimental and theoretical det...

Citation Formats

A. Baran, A. Guenel, and M. Balcı, “Synthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8 hexols (Bishomoinositols) as glycosidase inhibitors,” JOURNAL OF ORGANIC CHEMISTRY, pp. 4370–4375, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57615.