Enantiospecific total syntheses of kapakahines B and F.
Gram-scale, enantiospecific total syntheses of the anti-leukemia marine natural products kapakahines B and F have been completed. Two powerfully simplifying transformations have enabled the gram-scale synthesis of this natural product family: (1) an oxidative N-C bond-forming reaction that sets a key quaternary center with complete stereocontrol and (2) a unique strategy for the construction of twisted macrocycles via dynamic equilibration of complex late-stage intermediates.
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Timothy
T
Newhouse
Chad A
CA
Lewis
Phil S
PS
Baran
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D001688:Biological Products; D047028:Macrocyclic Compounds; D010456:Peptides, Cyclic; D000644:Quaternary Ammonium Compounds; C541864:kapakahine B; C476160:kapakahine F