title: Total synthesis of (+)-lyconadin A and related compounds via oxidative C-N bond formation.
abstract: The formation of carbon-nitrogen (C-N) bonds is a fundamental bond construction in organic synthesis and is indispensable for the synthesis of alkaloid natural products. In the context of the synthesis of the architecturally complex Lycopodium alkaloid lyconadin A, we have discovered a highly efficient oxidative C-N bond forming reaction that relies on the union of a nitrogen anion and a carbon anion. Empirical evidence amassed during our synthetic studies suggests that the mechanism of the C-N bond forming process encompasses polar as well as radical processes. Herein, we present our study of this novel C-N bond forming reaction and its application to the enantioselective total synthesis of lyconadin A and related derivatives.
authors: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors: Scott P
authors: SP
authors: West
authors: Alakesh
authors: A
authors: Bisai
authors: Andrew D
authors: AD
authors: Lim
authors: Raja R
authors: RR
authors: Narayan
authors: Richmond
authors: R
authors: Sarpong
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D002244:Carbon; D032502:Lycopodium / Q000737:chemistry; D009584:Nitrogen; D055601:Organic Chemistry Phenomena; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011083:Polycyclic Compounds; C435307:lyconadin A; D002244:Carbon; D009584:Nitrogen