A Concise Enantioselective Total Synthesis of (–)-Deoxoapodine

An organic chemistry minilecture on A Concise Enantioselective Total Synthesis of (–)-Deoxoapodine by Kei Yoshida, Kosuke Okada, Hirofumi Ueda, and Hidetoshi Tokuyama*. Highlights include an enantioselective bromocycization, a Pd promoted C-H activation/alkylation cascade and an oxidative transannular Mannich reaction Socials: Twitter: @SimplifyingSyn1 References: Angew. Chemie - Int. Ed. 2020, 59, 23089–23093 (This work) R. Inglesias, L. Diatta, Rev. CENIC, Cienc. Fis. 1975, 6, 135 (Isolation) , 16, 1908−1911 (bromocyclization) Science 2011, 334, 1681–1684 (bromocyclization) Tetrahedron 1985, 41, 4079–4094. (Keck Allylation) Tetrahedron 2017, 73, 4233–4258 (Ozonolysis) Tetrahedron 55 (1999) 13159-13170 (DMT-MM Coupling) J. Am. Chem. Soc. 2012, 134, 35, 14563–14572 (Norbornene Mediated C-H Activation) J. Am. Chem. Soc. 2017, 139, 8, 3153–3160 (Halide scavenger) Org. Lett. 2014, 16, 16, 4194–4197 (C-H Oxidation) Nature Chemistry. 2011, 3, pages 216–222 (C-H Oxidation) J. Am. Chem. Soc. 2001, 123, 26, 6327–6337 (C-H Oxidation) J. Am. Chem. Soc. 2018, 140, 43, 13988–14009 (C-H Oxidation)