Do anti-Bredt natural products exist? Olefin strain energy as a predictor of isolability

Krenske, Elizabeth H. and Williams, Craig M. (2015) Do anti-Bredt natural products exist? Olefin strain energy as a predictor of isolability. Angewandte Chemie International Edition, 54 36: 10608-10612. doi:10.1002/anie.201503822


 
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Author Krenske, Elizabeth H.
Williams, Craig M.
Title Do anti-Bredt natural products exist? Olefin strain energy as a predictor of isolability
Journal name Angewandte Chemie International Edition   Check publisher's open access policy
ISSN 1433-7851
1521-3773
Publication date 2015-09-01
Year available 2015
Sub-type Article (original research)
DOI 10.1002/anie.201503822
Open Access Status Not Open Access
Volume 54
Issue 36
Start page 10608
End page 10612
Total pages 6
Place of publication Weinheim, Germany
Publisher Wiley - VCH Verlag GmbH
Collection year 2016
Language eng
Formatted abstract
Bredt’s rule holds a special place in the realm of physical organic chemistry, but its application to natural products chemistry—the field in which the rule was originally formulated—is not well defined. Herein, the use of olefin strain (OS) energy as a readily calculated predictor of the stability of natural products containing a bridgehead alkene is introduced. Schleyer first used OS energies to classify parent bridgehead alkenes into “isolable”, “observable”, and “unstable” classes. OS calculations on natural products, using contemporary forcefield methods, unequivocally predict all structurally verified bridgehead alkene natural products to be “isolable”. Thus, when one assigns the structure of a putative bridgehead alkene natural product, an OS in the “observable” or “unstable” ranges is a red flag for error.
Keyword Anti Bredt
Bredt’s rule
Bridgehead olefins
Natural products
Strained molecules
Q-Index Code C1
Q-Index Status Confirmed Code
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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Citation counts: TR Web of Science Citation Count  Cited 3 times in Thomson Reuters Web of Science Article | Citations
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Created: Fri, 31 Jul 2015, 10:23:23 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences