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  • Synthesis of bishomoinositols and an entry for construction of a substituted 3-oxabicyclo[3.3.1]nonane skeleton.

Synthesis of bishomoinositols and an entry for construction of a substituted 3-oxabicyclo[3.3.1]nonane skeleton.

The Journal of organic chemistry (2012-01-11)
Arif Baran, Merve Bekarlar, Gökay Aydin, Mehmet Nebioglu, Ertan Şahin, Metin Balci
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Nonane, ReagentPlus®, 99%
Supelco
Nonane, analytical standard
Sigma-Aldrich
Nonane, anhydrous, ≥99%