title: Radical-mediated dimerization and oxidation reactions for the synthesis of complex alkaloids.
abstract: Concise and general strategies for radical-based dimerization of cyclotryptamine and cyclotryptophan derivatives in addition to radical-based oxidation of structurally complex diketopiperazines are discussed. The impact of these radical-based chemistries on the rapid generation of molecular  complexity is highlighted using representative examples from recent complex homodimeric alkaloid total syntheses. Additionally, a new and general strategy for radical-based directed heterodimerization of cyclotryptamine substructures via solvent-caged unsymmetrical diazene fragmentation  is discussed.
authors.affiliation: Massachusetts Institute of Technology, Departement of Chemistry, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Lathrop
authors.forename: Justin
authors.initials: J
authors.lastname: Kim
authors.forename: Mohammad
authors.initials: M
authors.lastname: Movassaghi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D019281:Dimerization; D005609:Free Radicals / Q000737:chemistry*; D008968:Molecular Conformation; D010084:Oxidation-Reduction
chemical_list: D000470:Alkaloids; D005609:Free Radicals