ol5b02965_si_001.pdf (2.49 MB)

Towards the Synthesis of Dihydrooxepino[4,3‑b]pyrrole-Containing Natural Products via Cope Rearrangement of Vinyl Pyrrole Epoxides

Download (2.49 MB)
journal contribution
posted on 18.12.2015 by Alex Cameron, Brendan Fisher, Nicholas Fisk, Jessica Hummel, Jonathan M. White, Elizabeth H. Krenske, Mark A. Rizzacasa
An approach to the dihydrooxepino­[4,3-b]­pyrrole core of diketopiperazine natural products which utilizes a vinyl pyrrole epoxide Cope rearrangement was investigated. It was found that an ester substituent on the epoxide was essential for the [3,3]-rearrangement to occur. Density functional calculations with M06-2X provided explanations for the effects of the pyrrole and ester groups on these rearrangements.