Synthesis of bishomoinositols and an entry for construction of a substituted 3-oxabicyclo[3.3.1]nonane skeleton.
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.
Department of Chemistry, Sakarya University, 54100 Sakarya, Turkey. abaran@sakarya.edu.tr
Arif
A
Baran
Merve
M
Bekarlar
Gökay
G
Aydin
Mehmet
M
Nebioglu
Ertan
E
Şahin
Metin
M
Balci
D000473:Alkanes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D007294:Inositol / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D055668:Photochemical Processes
D000473:Alkanes; D001643:Bridged Bicyclo Compounds; D007294:Inositol; C017573:nonane