936114-07-7Relevant academic research and scientific papers
Total synthesis of (-)-martinellic acid
Badarinarayana, Vivek,Lovely, Carl J.
, p. 2607 - 2610 (2007)
An enantioselective formal total synthesis of the pyrrolo[3,2-c]quinoline natural product martinellic acid has been achieved. The key steps involve a Pd-catalyzed aryl amidation reaction of a pyrroglutamate derivative, an intramolecular [3+2] azomethine ylide-alkene cycloaddition and a reductive ring opening reaction.
An asymmetric total synthesis of martinellic acid
Badarinarayana, Vivek,Mahmud, Hossen,Lovely, Carl J.
, p. 1082 - 1105 (2019/11/14)
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.
