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Paper | Regular issue | Vol 81, No. 11, 2010, pp.2523-2537
Published online, 14th September, 2010
DOI: 10.3987/COM-10-12010
Formal Total Synthesis of Enantiopure Tricyclic (S)-Myrmicarin Alkaloids 217, 215A and 215B

Marco Santarem, Corinne Vanucci-Bacqué,* and Gérard Lhommet*

*Department of Chemistry, IPCM, University of Paris VI, 4, Place Jussieu, F-75252 Paris Cedex 05, France

Abstract

We described herein a formal synthesis of the enantiopure tricyclic (4aS)-myrmicarin alkaloids 217, 215A and 215B owing to the obtention of a common pyrroloindolizidine intermediate, starting from a chiral cis-(2S,5R)-disubstituted pyrrolidine. An intramolecular one-pot aldolization-crotonization-aromatization process of a diketo indolizidine constitutes the key step for the formation of the pyrrole ring of the target compound.