11-Step and Scalable Total Synthesis of Hamigeran M Enabled by Five C−H Functionalizations

An organic chemistry minilecture on the Total Synthesis of Hamigeran M by Baiyang Jiang and Mingji Dai*. Highlights include multiple directed C-H activation reactions, a stereoselective hydrogen atom transfer reaction and Suzuki and Negishi cross-coupling reactions. SUPPORT THE CHANNEL ON PATREON: Socials: References: J. Am. Chem. Soc. 2021, 143, 48, 20084–20089 (This work) J. Org. Chem. 2015, 80, 1, 304–312 (isolation) Tetrahedron: Asymmetry. 2011, 22, 69-100 (Ketoester synthesis) J. Am. Chem. Soc. 2017, 139, 23, 7864–7871 (Cresol Borylation) J. Am. Chem. Soc. 2016, 138, 14, 4962–4971 (Hydrogen Atom Transfer) J. Am. Chem. Soc. 2014, 136, 4, 1300–1303 (Hydrogen Atom Transfer) Chem. Rev. 2016, 116, 15, 8912–9000 (Hydrogen Atom Transfer Review) Org. Lett. 2009, 11, 8, 1837–1840 (TMPZnCl·LiCl Reagent) Chem. Sci., 2013,4, 916-920 (Me4tBuPhos Pd G3 Catalyst) J. Am. Chem. Soc. 2011, 133, 48, 19310–19313 (Rh Borylation)