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.