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  • Title: Intramolecular 1,3-dipolar cycloaddition-mediated stereoselective synthesis of disubstituted cyclopentane: a simple model for the cyclopentane ring system of polycyclic oroidine alkaloids.
    Author: Fukahori Y, Takayama Y, Imaoka T, Iwamoto O, Nagasawa K.
    Journal: Chem Asian J; 2013 Jan; 8(1):244-50. PubMed ID: 23081863.
    Abstract:
    We present a diastereoselective synthesis of disubstituted cyclopentane 8 having a nitrogen-containing quaternary carbon center, which is found in axinellamine A (5) and related compounds. During this work, we found that the 1,3-dipolar cycloaddition product 24 immediately underwent intramolecular redox reaction at the newly formed morpholin-2-one moiety, thus affording disubstituted cyclopentane containing a tertiary amine (9) stereoselectively in good yield. The amine 9 was successfully converted into guanidine 31, which corresponds to 8, through iminium cation-enamine isomerization.
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