Total Synthesis of (−)-Peyssonnoside A

An organic chemistry minilecture on the 13-Step Total Synthesis of (−)-Peyssonnoside A by Bo Xu, Chang Liu, and Mingji Dai* It features some excellent metal catalysed C-C bond forming chemistry, including a Cu-catalysed asymmetric conjugate addition, a Pd- catalysed dearomative cyclization and Wittig reaction with the Lebel modification. 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, 19700−19703 (This work) J. Org. Chem. 2019, 84, 13, 8531–8541 (Isolation) Eur J Org Chem, 2012, 27, 5301–5306 (Cu-NHC catalyzed Michael addition) Org. Lett. 2014, 16, 118−12 (Cu-NHC catalyzed Michael addition) Eur. J. Org. Chem. 2015, 7460–7467 (Demethylation) Angew. Chem., Int. Ed. 2020,59, 8143−8147 (Dearomative Cyclisation) Angew. Chem., Int. , 54, 3033−3037 (Dearomative Cyclisation) J. Am. Chem. Soc. 2017, 139, 6, 2484–2503 (HAT Cyclisation) J. Am. Chem. Soc. 2014, 136, 1304−1307 (HAT Cyclisation) J. Am. Chem. Soc. 2004, 126, 1, 320–328 (Lebel Olefination) Angew. Chem., Int. Ed. 2021, 60, 8313−8320 (Studer’s anaerobic Mukaiyama hydration) J. Am. Chem. Soc. 2021, 143, 14083−14088 (Endgame)