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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
Metadata
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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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BibTeX
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.