Addition of carbonyl compounds to the cyclic olefins : synthesis of cyclitols

Download
2008
Altun, Yasemin
Cyclitols have attracted a great deal of attention in recent years owing to biological activities exhibited by them and also their usefulness in the synthesis of other natural products and pharmaceuticals. Carbasugars are also a derivative of cyclitols and they are cyclic monosaccharide analogues which posses CH2OH group in their structure. In this study, novel synthetic strategies leading to cyclitol derivatives were investigated and the synthesis of tetraol (72) and pentaol (73) derivatives containing CH2OH group were achieved successfully. Moreover, by the use of manganese(III) acetate oxidation reactions having considerable synthetic utilities in organic chemistry we developed new synthetic methodologies for the cyclitol derivatives. 1,3- and 1,4-Cyclohexadiene (71 and 10) were synthesized from easily available starting materials in order to be used as key compounds. The use of manganese(III) acetate oxidation reaction provides the creation of CH2OH group and one of the hydroxyl groups and the remaining hydroxyl groups were introduced into the key compounds by the use of singlet oxygen reaction. As a result of this, we had considerable advance in the synthesis of cyclitol derivatives.

Suggestions

The development of the novel synthesis for conduritols
Cantekin, Seda; Balcı, Metin; Department of Chemistry (2006)
Conduritols have attracted a great deal of attention in recent years owing to biological activities exhibited by them and also their usefulness in the synthesis of other natural products and pharmaceuticals. Conduritols show interesting inhibitor activity for some glycosidases and serve as important intermediates in the synthesis of inositols. In this study, novel synthetic strategies leading to highly functionalized cyclohexene derivative containing an aromatic ring, namely phenyl-substituted conduritol wa...
Reaction of propargyl aldehydes with hydrazinium salts: synthesis of ferrocenyl and Phenyl substituted pyrazoles
Pınar, Ayşe Nur; Zora, Metin; Department of Chemistry (2008)
Pyrazoles have been focus of a large number of investigations in the design and synthesis of novel biologically active agents that show remarkable medicinal activities. Although pyrazoles have been studied for over a century as an important class of heterocyclic compounds, they still continue to attract considerable attention due to the wide range of medicinal activities they possess. Recent studies have shown that combination of a ferrocenyl unit with structural features of pyrazoles can lead to products w...
Synthesis of 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-1H-pyrazoles by electrophilic cyclization
Karahan Dağ, Fulya; Zora, Metin; Department of Chemistry (2011)
Pyrazoles have been intensely studied in the design and synthesis of biologically active agents because they display considerable medicinal activities. Recent studies have shown that integration of a ferrocenyl unit with structural features of pyrazoles can result in the formation of the new products with enhanced or/and unexpected biological activity since several ferrocene derivatives have already been illustrated to be active against a number of tumors. Therefore, we have investigated the electrophilic c...
The synthesis of hydroxymethyl containing cyclitol derivatives
Kaya, Nihal; Balcı, Metin; Department of Chemistry (2009)
Cyclitols have attracted a great deal of attention in recent years because of diverse biological activities exhibited by them and also synthetic usefulness in the synthesis of other natural compounds or pharmaceuticals. The presence of hydroxymethyl groups in many cyclitols units building natural products is also attracting a remarkable attention. In this study, novel synthetic strategies leading to cyclitol derivatives including hydroxymethyl groups were investigated and the syntheses of bis-homoinositol d...
Development of new synthetic methodologies for indole derivatives
Kılıklı, Ahmet Alper; Balcı, Metin; Department of Chemistry (2010)
Synthesizing nitrogen containing heterocyclic compounds is one of the leading research areas throughout the organic chemistry due to their significant activities on biological systems. Among the various biologically active molecules, indole derivatives are of prime importance on the grounds of their proven clinical roles. Objective of this study is to synthesize new indole derivatives those may contribute treatment of several diseases like their analogues via a recently developed synthetic methodology. Besi...
Citation Formats
Y. Altun, “Addition of carbonyl compounds to the cyclic olefins : synthesis of cyclitols,” M.S. - Master of Science, Middle East Technical University, 2008.