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

Alex Cameron, Brendan Fisher, Nicholas Fisk, Jessica Hummel, Jonathan M. White, Elizabeth H. Krenske*, Mark A. Rizzacasa

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)5998-6001
Number of pages4
JournalOrganic Letters
Volume17
Issue number24
DOIs
Publication statusPublished - 2 Dec 2015
Externally publishedYes

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