Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors

Baran, Arif
Balcı, Metin
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. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.


Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton
BARAN, ARİF; Bekarlar, Merve; Aydin, Gokay; NEBİOĞLU, MEHMET; ŞAHİN, Ertan; Balcı, Metin (2012-02-03)
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 mechan...
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...
Enantioselective direct aldol reactions promoted by phosphine oxide aziridinyl phosphonate organocatalysts
Doğan, Özdemir (2015-12-15)
A series of phosphine oxide based chiral Lewis bases were screened as organocatalysts for silicon tetrachloride mediated direct asymmetric aldol reactions between cyclohexanone and various aromatic aldehydes. One of the phosphine oxide-aziridinyl phosphonate POAP-A Lewis bases formed the aldol products in up to 75% yield and with 65% ee.
Electrochemical copolymerization of thiophene containing pseudo-polyether cages with pyrrole
Cihaner, Atilla; Önal, Ahmet Muhtar (2006-01-01)
Conducting copolymers were synthesized via the electrochemical oxidation of pyrrole (Py) in the presence of the monomer 1,12-bis(2-thienyl)-2,5,8,11-tetraoxadodecane (1). The presence of monomer I in the electrolytic solution greatly changed the CV behavior of Py during its potensiodynamic polymerization. The electroactivity of poly(I-co-Py) increased with the increasing amount of I in the comonomer mixture. Copolymer films were prepared via constant potential electrolysis in an electrolytic solution contai...
Activity Comparison of MCM-41 and V-MCM-4 Catalysts for Ethanol Selective Oxidation and DRIFTS Analysis
Gucbilmez, Yesim; Doğu, Timur; BALCI, FATMA SUNA (2009-01-01)
The activity of a V-MCM-41 catalyst with a V/Si molar ratio of 0.04 was compared with the activity of a pure MCM-41 catalyst and some DRIFTS studies were performed in order to understand the mechanism of selective oxidation of ethanol. V-MCM-41 was found to be much more active than pure MCM-41, favouring the formation of high amounts of ethylene over 300 degrees C. MCM-41, on the other hand, was found to favour the formation of acetaldehyde over ethylene at all studied temperatures. It was shown by reaction...
Citation Formats
A. Baran and M. Balcı, “Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors,” JOURNAL OF ORGANIC CHEMISTRY, pp. 88–95, 2009, Accessed: 00, 2020. [Online]. Available: