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Sequential Nucleophilic Addition/Intramolecular Cycloaddition to Chiral Nonracemic Cyclic Nitrones: A Highly Stereoselective Approach to Polyhydroxynortropane Alkaloids
journal contribution
posted on 2011-05-20, 00:00 authored by Ignacio Delso, Tomás Tejero, Andrea Goti, Pedro MerinoTwo new polyhydroxylated nortropane analogues closely related with Calystegines have been prepared in excellent chemical yields and complete selectivity. A synthetic strategy based on consecutive nucleophilic allylation, oxidation, and intramolecular dipolar cycloaddition was developed. The formation of key intermediate cycloadducts were observed to take place through the recently confirmed thermally induceded 2-aza-Cope rearrangement of nitrones.
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selectivitySequentialpolyhydroxylated nortropane analoguesCalystegineStereoselective Approachchemical yieldsstrategyoxidationChiral Nonracemic Cyclic NitronesNucleophilicnucleophilic allylationcycloadductinducededintramolecular dipolar cycloadditionnitronePolyhydroxynortropane AlkaloidsTworearrangementformationCycloaddition
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