Total Synthesis of Cephalosporolide F

An organic chemistry minilecture on the ’The Stereoselective Total Synthesis of the Elusive Cephalosporolide F’ by Leonardo Xochicale-Santana, Omar Cortezano-Arellano, Bernardo A. Frontana-Uribe, Victor M. Jimenez-Pérez, and Fernando Sartillo-Piscil*. It features an efficient microwave reaction of glucose and Meldrum’s acid to create the core structure and a photoredox cyclization to form a challenging spiroketal. Total Synthesis of Leonuketal: Total Synthesis of Portimines A&B: Total Synthesis of Spirochensilide A (Chen and Yang) Total Synthesis of Spirochensilide A (Heretsch) SUPPORT THE CHANNEL ON PATREON: Socials: References: J. Org. Chem. 2023, 88, 7, 4880–4885 (This work) J. Chem. Soc., Perkin Trans.1 1985, 1, 843 (Discovery) Curr. Org. Chem. 2003, 7, 1461 (Chemistry of spiroketal systems) J. Carbohydr. Chem. 2000, 19, 1019 (Lactonisation with Meldrums Acid) Angew. Chem. Int. Ed. 2016, 55, 1872 –1875 (Photochemical radical generation) Chem. Rev. 1997, 97,3273(Spirocyclization selectivity rationale) Top. Curr. Chem. 2005, 263, 1. (Spirocyclization selectivity rationale) J. Chem. Phys. 2019, 150, 084104 (Spirocyclization selectivity rationale)