title: Enantioselective Total Synthesis of (-)-Martinellic Acid.
abstract: An enantioselective total synthesis of martinellic acid is described. The pyrroloquinoline alkaloid core is efficiently prepared from a quinoline, employing a method which relies on a newly developed Cu-catalyzed enantioselective alkynylation using the chiral imidazole-based biaryl P,N ligand StackPhos to establish the absolute stereochemistry. The remaining carbon atoms are then installed by means of a diastereoselective Pd-catalyzed decarboxylative allylation and the synthesis is completed after straightforward functional-group manipulation. This new synthetic method enables the most concise enantioselective synthesis of this important class of molecules to date.
authors.affiliation: Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611 (USA).
authors.forename: Mukesh
authors.initials: M
authors.lastname: Pappoppula
authors.affiliation: Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611 (USA). aponick@chem.ufl.edu.
authors.forename: Aaron
authors.initials: A
authors.lastname: Aponick
mesh_terms: D002384:Catalysis; D011758:Pyrroles / Q000138:chemical synthesis*; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011758:Pyrroles; D011804:Quinolines; C432345:martinellic acid
keywords: alkynes; copper; martinellic acid; natural products; total synthesis