Enantioselective Total Synthesis of (−)‐Martinellic Acid |
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Authors: | Mukesh Pappoppula Prof. Aaron Aponick |
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Affiliation: | Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, FL 32611 (USA) |
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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. |
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Keywords: | alkynes copper martinellic acid natural products total synthesis |
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