Article 2022 · 4 atıf

Stereoselective synthesis of novel bis-homoinositols with bicyclo[4.2.0] octane motifs

Barotcu, Aysenur Zeren, Karanfil, Abdullah, Sahin, Ertan, Kelebekli, Latif

Özet

Starting from cyclooctatetraene, bis-homoconduritols with cis-inositol and allo-inositol (or bicyclo[4.2.0]octane motif) structures were synthesized. Photooxygenation of trans-7,8-dibromo-bicyclo[4.2.0]octa-2,4-diene allowed the preparation of tricyclic endoperoxide. The compound diacetate was obtained by reduction of endoperoxide with thiourea followed by acetylation reaction. Removal of halides with zinc dust in acetic acid yielded the diendiacetate, a key compound of the designed molecules. OsO4 oxidation of diendiacetate followed by acetylation gave the corresponding hexaacetates. Finally, the novel desired bis-homoinositols were obtained in high yield by the ammonolysis of acetate groups. The structures of all synthesized compounds were characterized by spectroscopic methods.

Anahtar Kelimeler

Inositol Bis -homoinositol Bis -homoconduritol Polycyclitol bicyclo[4 2 0]octane STEREOSPECIFIC SYNTHESIS MOLECULAR COMPLEXITY INOSITOL CARBASUGARS INHIBITION GENERATION ANALOG

WoS Kategorileri

Biochemistry & Molecular Biology Chemistry, Applied Chemistry, Organic

Sürdürülebilir Kalkınma Amaçları

Sağlık ve Kaliteli Yaşam

Künye

Dergi: CARBOHYDRATE RESEARCH
Yıl: 2022
Cilt: 519
ISSN: 0008-6215
eISSN: 1873-426X
DOI: 10.1016/j.carres.2022.108611
WoS UID: WOS:000817872400006

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