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Paper | Special issue | Vol 95, No. 2, 2017, pp.1082-1105
Published online, 21st February, 2017
DOI: 10.3987/COM-16-S(S)81
An Asymmetric Total Synthesis of Martinellic Acid

Vivek Badarinarayana, Hossen Mahmud, and Carl J. Lovely*

*Department of Chemistry and Biochemistry, University of Texas Arlington, Arlington, TX76019, U.S.A.

Abstract

We describe an asymmetric total synthesis of the pyrrolo[3,2-c]quinoline natural product martinellic acid starting from pyrroglutamic acid. A convergent strategy involving a Pd-catalyzed aryl amination reaction of a chiral, non-racemic pyrrolidine derivative incorporates the C2-chiral center which controls the remaining two stereocenters. Elaboration of this adduct through a Grieco-elimination sets the stage for a diastereoselective intramolecular [3+2] azomethine ylide-alkene cycloaddition and the construction of the remaining two chiral centers. Elaboration of the cycloadduct and incorporation the prenyl guanidine units delivered martinellic acid after removal of the protecting groups.