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Issue 1, 2016
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Stereoselective total synthesis of (−)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C–C bond formation

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Abstract

An efficient stereoselective synthesis of the nuphar alkaloid, (−)-nupharamine, is reported. The key features include the Lewis acid catalyzed reaction of an α-chlorosulfide with a silyl ketene acetal for C–C bond formation, creation of the stereocenter at C2 by a diastereoselective reaction of allyl indium with a sulfinimine and reductive amination for the introduction of the C6 stereocenter of the piperidine ring.

Graphical abstract: Stereoselective total synthesis of (−)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C–C bond formation

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The article was received on 21 Aug 2015, accepted on 13 Oct 2015 and first published on 14 Oct 2015


Article type: Paper
DOI: 10.1039/C5OB01750E
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Org. Biomol. Chem., 2016,14, 131-137

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    Stereoselective total synthesis of (−)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C–C bond formation

    S. Raghavan and S. Rajendar, Org. Biomol. Chem., 2016, 14, 131
    DOI: 10.1039/C5OB01750E

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