936114-10-2Relevant articles and documents
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.
Total synthesis of (-)-martinellic acid
Badarinarayana, Vivek,Lovely, Carl J.
, p. 2607 - 2610 (2007/10/03)
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.
