Towards the synthesis of dihydrooxepino[4,3-b]pyrrole-containing natural products via cope rearrangement of vinyl pyrrole epoxides

Cameron, Alex, Fisher, Brendan, Fisk, Nicholas, Hummel, Jessica, White, Jonathan M., Krenske, Elizabeth H. and Rizzacasa, Mark A. (2015) Towards the synthesis of dihydrooxepino[4,3-b]pyrrole-containing natural products via cope rearrangement of vinyl pyrrole epoxides. Organic Letters, 17 24: 5998-6001. doi:10.1021/acs.orglett.5b02965


Author Cameron, Alex
Fisher, Brendan
Fisk, Nicholas
Hummel, Jessica
White, Jonathan M.
Krenske, Elizabeth H.
Rizzacasa, Mark A.
Title Towards the synthesis of dihydrooxepino[4,3-b]pyrrole-containing natural products via cope rearrangement of vinyl pyrrole epoxides
Formatted title
Towards the synthesis of dihydrooxepino[4,3-b]pyrrole-containing natural products via cope rearrangement of vinyl pyrrole epoxides
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7052
1523-7060
Publication date 2015-12-02
Year available 2015
Sub-type Article (original research)
DOI 10.1021/acs.orglett.5b02965
Open Access Status Not Open Access
Volume 17
Issue 24
Start page 5998
End page 6001
Total pages 4
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Formatted 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.
Keyword Chemistry, Organic
Chemistry
Q-Index Code C1
Q-Index Status Provisional Code
Grant ID FT120100632
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2016 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 04 Dec 2015, 20:49:01 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences