Deaminative ring contraction for the synthesis of polycyclic heteroaromatics: a concise total synthesis of toddaquinoline
Emily K. Kirkeby, Zachary Schwartz, Myles A. Lovasz, Andrew G. Roberts
Abstract
methylation of a biaryl-linked dihydroazepine to form a cyclic ammonium cation that undergoes a base-induced [1,2]-Stevens rearrangement/dehydroamination sequence. The presence of pseudosymmetry guides the retrosynthetic analysis of pyridyl-containing polycyclic heteroaromatics, enabling their construction by the reductive cyclization and deaminative contraction of tertiary amine precursors.
Topics & Concepts
Total synthesisChemistryContraction (grammar)Ring (chemistry)StereochemistryCombinatorial chemistryOrganic chemistryBiologyEndocrinologyChemical synthesis and alkaloidsAxial and Atropisomeric Chirality SynthesisSynthetic Organic Chemistry Methods