title: Scalable, stereocontrolled total syntheses of (±)-axinellamines A and B.
abstract: The development of a simple, efficient, scalable, and stereocontrolled synthesis of a common intermediate en route to the axinellamines, massadines, and palau'amine is reported. This completely new route was utilized to prepare the axinellamines on a gram scale. In a more general sense, three distinct and enabling methodological advances were made during these studies: (1) an ethylene glycol-assisted Pauson-Khand cycloaddition reaction, (2) a Zn/In-mediated Barbier-type reaction, and (3) a TfNH(2)-assisted chlorination-spirocyclization.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.
authors.forename: Shun
authors.initials: S
authors.lastname: Su
authors.forename: Rodrigo A
authors.initials: RA
authors.lastname: Rodriguez
authors.forename: Phil S
authors.initials: PS
authors.lastname: Baran
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000191:economics / Q000379:methods*; D006146:Guanidines / Q000138:chemical synthesis; D007093:Imidazoles / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D006146:Guanidines; D007093:Imidazoles; D011758:Pyrroles; D013141:Spiro Compounds; C520388:axinellamine; C478874:massadine; C438976:palau'amine