Ring opening of cyclic ethers by sulfuric acid - Acetic anhydride
Cyclic ethers such as tetrahydrofuran or tetrahydropyran were easily cleaved at room temperature by sulfuric acid - acetic anhydride providing the corresponding diacetoxyalkanes in good yield. The ring opening was applicable to saturated cyclic ethers, regardless of the presence of substituent groups.
A synthesis of (-)-tashiromine and formal synthesis of (+)-tashiromine utilizing a highly enantioselective pyrrole/cobaloxime π-cation cyclization
Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime (13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime π-cation onto the pyrrole ring to provide 6-exo cyclization product (14) in 95% yield. This cyclization is highly enantioselective. It is applied to a synthesis of highly enantioenriched (-)-tashiromine, (-)-21, and a formal synthesis of (+)-tashiromine.
Gage, Jennifer L.,Branchaud, Bruce P.
p. 7007 - 7010
(2007/10/03)
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