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Issue 5, 2012
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Total synthesis of the monoterpenoid alkaloid (±)-tangutorine

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A novel approach to a formal total synthesis of the monoterpenoid indole alkaloid (±)-tangutorine has been developed starting from an α,β-unsaturated cyclic dehydroamino ester. Synthesis of the rather unusual trans-substituted 2,3-indoloquinolizidine substructure was accomplished viaCu(II)-mediated conjugate addition and organozinc/copper coupling as the key steps, thereby setting the stage for ring-closing metathesis to produce the quinolone substructure. Finally, Bischler–Napieralski cyclization gave rise to the pentacyclic system of (±)-tangutorine thereby realizing a formal synthesis in an overall yield of 5.2% in eight consecutive steps.

Graphical abstract: Total synthesis of the monoterpenoid alkaloid (±)-tangutorine

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The article was received on 07 Sep 2011, accepted on 10 Nov 2011 and first published on 16 Nov 2011

Article type: Paper
DOI: 10.1039/C1OB06539D
Citation: Org. Biomol. Chem., 2012,10, 945-951

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    Total synthesis of the monoterpenoid alkaloid (±)-tangutorine

    S. (. A. M. W. van den Broek, J. G. H. Lemmers, F. L. van Delft and F. P. J. T. Rutjes, Org. Biomol. Chem., 2012, 10, 945
    DOI: 10.1039/C1OB06539D

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