10.1021/ol070563g.s001 Yefen Zou Yefen Zou Chun-Hsing Chen Chun-Hsing Chen Christopher D. Taylor Christopher D. Taylor Bruce M. Foxman Bruce M. Foxman Barry B. Snider Barry B. Snider Formal Synthesis of (±)-Platensimycin American Chemical Society 2007 tricyclic bicyclic dione cyclized PlatensimycinReductive synthesis MnO 2 SeO 2 enone 2 Formal Synthesis cyclization Allylic oxidation platensimycin dibromopropene methoxy tetracyclic alkene 13 equilibrium mixture alkylation Radical 2007-04-26 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Formal_Synthesis_of_Platensimycin/3011221 Reductive alkylation of 5-methoxy-1-tetralone (<b>6</b>) with 2,3-dibromopropene gave an equilibrium mixture of bicyclic diones <b>7</b> (51%) and <b>8</b> (35%). Radical cyclization of <b>7</b> afforded tricyclic dione <b>5</b> (84%), which was reduced, cyclized, and dehydrated to give tetracyclic alkene <b>13</b> in 63% yield. Allylic oxidation of <b>13</b> with SeO<sub>2</sub> and activated MnO<sub>2</sub> afforded enone <b>2</b> in 85% yield, thereby completing a short formal synthesis of (±)-platensimycin.