Jump to main content
Jump to site search

Issue 5, 2012
Previous Article Next Article

Total synthesis of the monoterpenoid alkaloid (±)-tangutorine

Author affiliations

Abstract

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

Back to tab navigation

Supplementary files

Publication details

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
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements