Cascade Approach to Stereoselective Polycyclic Ether Formation: Epoxides as Trapping Agents in the Transposition of Allylic Alcohols


  • This work was supported by grants from the National Institutes of Health (P50-GM06082) and the National Science Foundation (CHE-1151979). We thank Dr. Steve Geib for crystallographic analyses, and Dr. Damodaran Krishnan and Sage Bowser for assistance with NMR experiments.


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Complexity from simplicity: Polycyclic ethers are synthesized by cascade reactions involving the use of epoxides as electrophilic traps in the transposition of allylic alcohols. Stereogenic centers are created by functionalizing prochiral sites under thermodynamic control, and remote stereoinduction can be achieved through the use of ketones as conduits.