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.