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

A Cameron; B Fisher; N Fisk; J Hummel; JM White; EH Krenske; MA Rizzacasa

Journal article

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

A Cameron, B Fisher, N Fisk, J Hummel, JM White, EH Krenske, MA Rizzacasa

Organic Letters | AMER CHEMICAL SOC | Published : 2015

DOI: 10.1021/acs.orglett.5b02965

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.

University of Melbourne Researchers

Jonathan White Author

Mark Rizzacasa Author

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X-ray Molecular Structure Elucidation Facility (MSEF)

X-ray diffraction plays a key role in identification and molecular characterization. X-ray techniques are the single most widely used analyt..

Grants

Awarded by National Computational Infrastructure

Funding Acknowledgements

We thank the Australian Research Council-Discovery Grants Scheme and Future Fellowships Scheme (FT120100632 to E.H.K) for funding, and the Australian National Computational Infrastructure National Facility for computer resources.