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Issue 11, 2011
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Intermolecular radical addition to N-acylhydrazones as a stereocontrol strategy for alkaloid synthesis: formal synthesis of quinine

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Abstract

Stereocontrolled Mn-mediated radical addition of alkyl iodides to chiral N-acylhydrazones enables strategic C–C bond disconnection of chiral amines. This strategy was examined in the context of a total synthesis of quinine, generating new findings of functional group compatibility leading to a revised strategy. Completion of a formal synthesis of quinine is presented, validating the application of Mn-mediated radical addition as a useful new C–C bond construction method for alkaloid synthesis. The Mn-mediated addition generates the chiral amine substructure of quinine with complete stereocontrol. Subsequent elaboration includes two successive ring closures to forge the azabicyclo[2.2.2]octane ring system of quincorine, linked to quinine through two known reactions.

Graphical abstract: Intermolecular radical addition to N-acylhydrazones as a stereocontrol strategy for alkaloid synthesis: formal synthesis of quinine

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Publication details

The article was received on 10 Feb 2011, accepted on 08 Mar 2011 and first published on 09 Mar 2011


Article type: Communication
DOI: 10.1039/C1OB05219E
Citation: Org. Biomol. Chem., 2011,9, 4039-4043
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    Intermolecular radical addition to N-acylhydrazones as a stereocontrol strategy for alkaloid synthesis: formal synthesis of quinine

    G. K. Friestad, A. Ji, C. S. Korapala and J. Qin, Org. Biomol. Chem., 2011, 9, 4039
    DOI: 10.1039/C1OB05219E

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