Total synthesis of piericidin A1. Application of a modified Negishi carboalumination-nickel-catalyzed cross-coupling.
A total synthesis of the mitochondrial complex I inhibitor piericidin A1 is described. It features a unique strategy for the key disconnection, highlighting a modified Negishi carboalumination/Ni-catalyzed cross-coupling on a polyenyne precursor.
Lipshutz
Bruce H
BH
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA. lipshutz@chem.ucsb.edu
Amorelli
Benjamin
B
D017607:Aluminum Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D017606:Chlorine Compounds / Q000138:chemical synthesis / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010847:Picolines / Q000138:chemical synthesis / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
D017607:Aluminum Compounds; D017606:Chlorine Compounds; D003432:Cross-Linking Reagents; D010847:Picolines; D011725:Pyridines; D002244:Carbon; D009532:Nickel; C100213:piericidin A