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Issue 33, 2012
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Enantioselective approach to functionalized quinolizidines: synthesis of (+)-julandine and (+)-cryptopleurine

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Abstract

An efficient synthesis of functionalized quinolizidines was developed from an enantiomerically enriched γ-nitroketone, which is easily prepared by an organocatalytic ketonenitroalkene Michael addition. Oxidative ring expansion of the nitroketone followed by reductive ring-opening leads to a suitably functionalized nitrodiol which is an intermediate to the title compounds.

Graphical abstract: Enantioselective approach to functionalized quinolizidines: synthesis of (+)-julandine and (+)-cryptopleurine

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Publication details

The article was received on 07 Apr 2012, accepted on 21 Jun 2012 and first published on 22 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25689D
Citation: Org. Biomol. Chem., 2012,10, 6776-6784
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    Enantioselective approach to functionalized quinolizidines: synthesis of (+)-julandine and (+)-cryptopleurine

    S. V. Pansare and R. Dyapa, Org. Biomol. Chem., 2012, 10, 6776
    DOI: 10.1039/C2OB25689D

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