Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton

Date

2012-02-03

Author

BARAN, ARİF
Bekarlar, Merve
Aydin, Gokay
NEBİOĞLU, MEHMET
ŞAHİN, Ertan
Balcı, Metin

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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

Subject Keywords

Cotpp-catalyzed reaction, Cost-effective catalyst, D-chiro-inositol, Stereoselective-synthesis, Enantiomerically pure, Biological evaluation, Convenient synthesis, Concise synthesis, Norbornyl route

URI

https://hdl.handle.net/11511/52488

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo202494v

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

A. BARAN, M. Bekarlar, G. Aydin, M. NEBİOĞLU, E. ŞAHİN, and M. Balcı, “Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton,” JOURNAL OF ORGANIC CHEMISTRY, pp. 1244–1250, 2012, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/52488.