Department of Chemistry, Sakarya University, 54100 Sakarya, Turkey.
J Org Chem. 2012 Feb 3;77(3):1244-50. doi: 10.1021/jo202494v. Epub 2012 Jan 12.
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.
1,3,3a,7a-四氢-2-苯并呋喃被用作合成各种双氢肌醇衍生物的关键化合物。该二烯经历环氧化反应，进一步官能化二烯单元。所得双环氧化物在水存在下与酸进行开环反应。合成了各种双氢肌醇。然而，当反应在醋酸酐存在下进行时，形成了取代的 3-氧杂双环[3.3.1]壬烷骨架。讨论了产物形成的机制。
