Journal article
Synthesis, characterization and reactivity of complex tricyclic oxonium ions, proposed intermediates in natural product biosynthesis
- Abstract:
- Reactive intermediates frequently play significant roles in the biosynthesis of numerous classes of natural products although the direct observation of these biosynthetically relevant species is rare. We present here direct evidence for the existence of complex, thermally unstable, tricyclic oxonium ions that have been postulated as key reactive intermediates in the biosyn-thesis of numerous halogenated natural products from Laurencia species. Evidence for their existence comes from full characterization of these oxonium ions by low temperature NMR spectroscopy supported by DFT calculations, coupled with the direct generation of ten natural products on exposure of the oxonium ions to various nucleophiles.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, 1.5MB, Terms of use)
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- Publisher copy:
- 10.1021/jacs.9b07438
Authors
- Publisher:
- American Chemical Society
- Journal:
- Journal of the American Chemical Society More from this journal
- Volume:
- 141
- Issue:
- 40
- Pages:
- 15951-15962
- Publication date:
- 2019-09-27
- Acceptance date:
- 2019-09-08
- DOI:
- EISSN:
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1520-5126
- ISSN:
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0002-7863
- Language:
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English
- Keywords:
- Pubs id:
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pubs:1052637
- UUID:
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uuid:0188aa06-1672-434d-a33b-9c6862ff937a
- Local pid:
-
pubs:1052637
- Source identifiers:
-
1052637
- Deposit date:
-
2019-09-13
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2019
- Rights statement:
- © 2019 American Chemical Society
- Notes:
- This is the accepted manuscript version of the article. The final version is available from American Chemical Society at: https://doi.org/10.1021/jacs.9b07438
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