Show/Hide Menu
Hide/Show Apps
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Open Access Guideline
Open Access Guideline
Postgraduate Thesis Guideline
Postgraduate Thesis Guideline
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Guides
Guides
Thesis submission
Thesis submission
MS without thesis term project submission
MS without thesis term project submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Supporting Information
Supporting Information
General Information
General Information
Copyright, Embargo and License
Copyright, Embargo and License
Contact us
Contact us
Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton
Date
2012-02-03
Author
BARAN, ARİF
Bekarlar, Merve
Aydin, Gokay
NEBİOĞLU, MEHMET
ŞAHİN, Ertan
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
219
views
0
downloads
Cite This
1,3,3a,7a-Tetrahydro-2-benzofuran was used as key compound for the synthesis of various bishomoinositol derivatives. The diene was subjected to an epoxidation reaction for further functionalization of the diene unit. The bisepoxide obtained was submitted to a ring-opening reaction with acid in the presence of water. Various bishomoinositols were synthesized. However, when the reaction was carried out in the presence of acetic anhydride, a substituted 3-oxabicyclo[3.3.1]nonane skeleton was formed. The mechanism of the formation of the products is discussed
Subject Keywords
Cotpp-catalyzed reaction
,
Cost-effective catalyst
,
D-chiro-inositol
,
Stereoselective-synthesis
,
Enantiomerically pure
,
Biological evaluation
,
Convenient synthesis
,
Concise synthesis
,
Norbornyl route
URI
https://hdl.handle.net/11511/52488
Journal
JOURNAL OF ORGANIC CHEMISTRY
DOI
https://doi.org/10.1021/jo202494v
Collections
Graduate School of Natural and Applied Sciences, Article
Suggestions
OpenMETU
Core
Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors
Baran, Arif; Balcı, Metin (2009-01-02)
For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. T...
Synthesis and characterization of Ba/MCM-41
Kaya, Emine; Oktar, Nuray; Karakaş, Gürkan; Murtezaoglu, Kirali (2010-01-01)
Mesoporous Ba/MCM-41 type materials (Ba/MCM-41) with high Ba/Si molar ratios between 0.025 and 0.1 were synthesized by direct hydrothermal synthesis. The samples were characterized by XRD, nitrogen adsorption, TGA-DTA, FTIR, SEM-EDS, and TEM techniques. BET surface areas of samples with various Ba loadings were found between 722 and 931 m(2)/g with 28 A average pore size, which is consistent with the pore size of 30 A for pure MCM-41 samples synthesized by the same procedure. The crystal structures of synth...
Synthesis and biological evaluation of optically active conjugated gamma- and delta-lactone derivatives
ŞARDAN, Melis; Sezer, Serdar; GUNEL, Aslihan; AKKAYA, MAHİNUR; Tanyeli, Cihangir (2012-09-15)
An efficient synthesis of racemic and both enantiomeric forms of heteroaryl substituted gamma- and delta-lactone derivatives derived from allyl and homoallyl alcohol backbones has been accomplished via ring closing metathesis reaction. 2-Heteroaryl substituted allyl and homoallyl alcohols have been efficiently resolved through enzymatic method with high ee (97-99%) and known stereochemistry. Antimicrobial and antioxidant activities of target lactones were evaluated.
Synthesis of Pyrazoles via Cul-Mediated Electrophilic Cyclizations of alpha,beta-Alkynic Hydrazones
Zora, Metin (2011-11-18)
Synthesis of pyrazoles via electrophilic cyclization of alpha,beta-alkynic hydrazones by copper(I) iodide is described. When treated with copper(I) iodide in the presence of triethylamine in refluxing acetonitrile, alpha,beta-alkynic hydrazones, prepared readily from hydrazines and propargyl aldehydes and ketones, undergo electrophilic cyclization to afford pyrazole derivatives in good to excellent yields. The reaction appears to be general for a variety of alpha,beta-alkynic hydrazones and tolerates the pr...
Synthesis of ferrocenyl quinones and ferrocenyl based burning rate catalysts
Açıkalın, Serdar; Zora, Metin; Department of Chemistry (2003)
Recently, considerable interest has been devoted to the synthesis of new ferrocene derivatives since properly functionalized ferrocene derivatives could be potential antitumor substances. For this purpose, we have investigated the synthesis of ferrocenyl quinones starting from squaric acid. Thermolysis of ferrocenylsubstituted cyclobutenones, which have been prepared from ferrocenyl cyclobutenediones and alkenyllithiums, affords hydroquinones, which furnish, upon oxidation, ferrocenyl quinones. Ferrocenyl c...
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
A. BARAN, M. Bekarlar, G. Aydin, M. NEBİOĞLU, E. ŞAHİN, and M. Balcı, “Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton,”
JOURNAL OF ORGANIC CHEMISTRY
, pp. 1244–1250, 2012, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/52488.