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

doi:10.1021/acs.orglett.5b02965

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 journal › Article › Academic › peer-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 language	English
Pages (from-to)	5998-6001
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.5b02965
Publication status	Published - 2 Dec 2015
Externally published	Yes

Funding

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.

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10.1021/acs.orglett.5b02965

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

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.",

author = "Alex Cameron and Brendan Fisher and Nicholas Fisk and Jessica Hummel and White, \{Jonathan M.\} and Krenske, \{Elizabeth H.\} and Rizzacasa, \{Mark A.\}",

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doi = "10.1021/acs.orglett.5b02965",

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AU - Cameron, Alex

AU - Fisher, Brendan

AU - Fisk, Nicholas

AU - Hummel, Jessica

AU - White, Jonathan M.

AU - Krenske, Elizabeth H.

AU - Rizzacasa, Mark A.

PY - 2015/12/2

Y1 - 2015/12/2

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AB - 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.

UR - https://www.scopus.com/pages/publications/84952657572

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IS - 24

ER -

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

Abstract

Funding

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