Angew Chem Int Ed Engl 2017 Sep 19. Epub 2017 Sep 19.
Seoul National University, Department of Chemistry, Gwanak-1 Gwanak-ro,, Gwanak-gu,, 151-742, Seoul, KOREA, REPUBLIC OF.
Here we report asymmetric total syntheses of communesin F and a putative member of the communesin family of bis-aminal alkaloid natural products. The successful strategy featured the invention of an asymmetric organocatalytic reaction to unify two oxindole subunits, a Ti(OiPr)4-mediated dehydrative skeletal rearrangement, and a late-stage Pd(OAc)2-catalyzed directed CH-alkenylation reaction. Collectively, the synthetic technologies disclosed herein enabled the preparation of a late-stage polycyclic intermediate catered for the synthesis of both naturally occurring and designed communesins. Read More