Diastereoselective Total Synthesis of (±)‐Toxicodenane A

• DOI: 10.1002/ejoc.201701219
• Publication Date: 2017-10-17T08:12:39Z
• Authors: Toyoharu Kobayashi; Kotono Yamanoue; Hideki Abe; Hisanaka Ito
• Keywords: Desymmetrization; Dimedone; Moiety; Diene; Salt metathesis reaction

The first total synthesis of tricyclic sesquiterpene (±)‐toxicodenane A has been accomplished. This synthetic work was completed in 12 steps from dimedone through diastereoselective reductive desymmetrization 2,2‐disubstituted 5,5‐dimethylcyclohexane‐1,3‐dione, stereocontrolled allylation, ring‐closing metathesis a diene compound to yield bicyclic compounds that bear seven‐membered ring, and construction the oxygen‐bridged moiety neighboring group assisted ring‐opening reaction an epoxide as key steps.