Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation
Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. He...
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| Published in | Angewandte Chemie International Edition Vol. 58; no. 21; pp. 7107 - 7112 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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Wiley Subscription Services, Inc
20.05.2019
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| Edition | International ed. in English |
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| Abstract | Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen‐substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.
Computationary, my dear Watson! The amalgamation of olefin strain energy (OSE) and DU8+ analysis brings to the fore a powerful combination of in silico methods that can be deployed in concert by those undertaking natural product structure determination. |
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| AbstractList | Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen‐substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.
Computationary, my dear Watson! The amalgamation of olefin strain energy (OSE) and DU8+ analysis brings to the fore a powerful combination of in silico methods that can be deployed in concert by those undertaking natural product structure determination. Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen‐substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures. Abstract Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen‐substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures. |
| Author | Krenske, Elizabeth H. Williams, Craig M. Kutateladze, Andrei G. |
| Author_xml | – sequence: 1 givenname: Andrei G. orcidid: 0000-0003-3066-517X surname: Kutateladze fullname: Kutateladze, Andrei G. email: andrei.kutateladze@du.edu organization: University of Denver – sequence: 2 givenname: Elizabeth H. orcidid: 0000-0003-1911-0501 surname: Krenske fullname: Krenske, Elizabeth H. email: e.krenske@uq.edu.au organization: University of Queensland – sequence: 3 givenname: Craig M. orcidid: 0000-0002-3834-7398 surname: Williams fullname: Williams, Craig M. email: c.williams3@uq.edu.au organization: University of Queensland |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31017378$$D View this record in MEDLINE/PubMed |
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| Keywords | anti-Bredt olefins bridgehead double bonds natural products Bredt rule reassignments |
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| SubjectTerms | anti-Bredt olefins Bredt rule bridgehead double bonds Chemists Natural products NMR Nuclear magnetic resonance Organic chemistry reassignments |
| Title | Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation |
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