Total Synthesis of Aberrarone

An organic chemistry minilecture on the Enantioselective Total Synthesis of ( )-Aberrarone by Willi M. Amberg and Erick M. Carreira*. It features a remarkable cyclization cascade that forms four rings and six stereocentres in one step. SUPPORT THE CHANNEL ON PATREON: NMR Spectroscopy in music: J. New Music Res. 2021, 50:5, 487-501 Socials: References: J. Am. Chem. Soc. 2022, 144, 26, 11574–11579 (This work) . Chem. 2009, 74, 7581−7584 (Isolation) Tetrahedron 2015, 71, 5918−5924 (studies towards the construction of the ring system) J. Am. Chem. Soc. 2000, 122, 8, 1806–1807 (Alkyne addition) J. Am. Chem. Soc., 2006,128, 1442–1443 (Meyer Schuster) J. Am. Chem. Soc. 2005, 127, 48, 16804–16805 (Meyer Schuster) Chem. Sci., 2019,10, 8219-8223 (Cyclization Cascade) Org. Lett. 2007, 9, 11, 2207–2209 (Au Catalysed cyclopropanation) Chem. Rev. 2021, 121, 14, 8613–8684 (Review on Au catalyzed synthesis of small rings) J. Am. Chem. Soc. 1976, 98, 1, 300–301 (Riley oxidation mechanism) 0:00 Introduction 1:03 Strategy: Cyclization Cascade 1:38 Alkyne Addition 2:11 Deprotection 2:15 Acetylation 2:35 Alkylation 3:01 Xanthate Formation 3:17 Barton-McCombie Deoxygenation 3:50 Triflate Formation 4:16 Sonogashira Coupling 4:54 Parikh-Doering Oxidation 6:55 Reduction 7:06 Reductive Ring Opening 7:58 Riley Oxidation