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Issue 54, 2014
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A gram-scale route to phlegmarine alkaloids: rapid total synthesis of (−)-cermizine B

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Abstract

The synthesis of the Lycopodium alkaloid (−)-cermizine B (1), which establishes its absolute configuration, is achieved by combining asymmetric organocatalysis and an uninterrupted eight-step reaction sequence, followed by a final reduction step. This “pot-economy” strategy provides access to the cis-phlegmarine stereoparent embedded in 1 for the first time, rapidly and on a gram-scale.

Graphical abstract: A gram-scale route to phlegmarine alkaloids: rapid total synthesis of (−)-cermizine B

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Publication details

The article was received on 06 Mar 2014, accepted on 03 Apr 2014 and first published on 03 Apr 2014


Article type: Communication
DOI: 10.1039/C4CC01708K
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Chem. Commun., 2014,50, 7099-7102

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    A gram-scale route to phlegmarine alkaloids: rapid total synthesis of (−)-cermizine B

    B. Bradshaw, C. Luque-Corredera and J. Bonjoch, Chem. Commun., 2014, 50, 7099
    DOI: 10.1039/C4CC01708K

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