Total Synthesis of Naphterpin and Marinone Natural Products
Publication type: Journal Article
Publication date: 2019-09-24
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
31549845
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6π-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.
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Metrics
27
Total citations:
27
Citations from 2024:
5
(18.52%)
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MLA
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GOST
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Murray L. A. M. et al. Total Synthesis of Naphterpin and Marinone Natural Products // Organic Letters. 2019. Vol. 21. No. 20. pp. 8312-8315.
GOST all authors (up to 50)
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Murray L. A. M., Fallon T. L., Sumby C. J., George J. R. Total Synthesis of Naphterpin and Marinone Natural Products // Organic Letters. 2019. Vol. 21. No. 20. pp. 8312-8315.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.9b03095
UR - https://doi.org/10.1021/acs.orglett.9b03095
TI - Total Synthesis of Naphterpin and Marinone Natural Products
T2 - Organic Letters
AU - Murray, Lauren A M
AU - Fallon, Thomas L.
AU - Sumby, Christopher J.
AU - George, Jonathan R.
PY - 2019
DA - 2019/09/24
PB - American Chemical Society (ACS)
SP - 8312-8315
IS - 20
VL - 21
PMID - 31549845
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Murray,
author = {Lauren A M Murray and Thomas L. Fallon and Christopher J. Sumby and Jonathan R. George},
title = {Total Synthesis of Naphterpin and Marinone Natural Products},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.orglett.9b03095},
number = {20},
pages = {8312--8315},
doi = {10.1021/acs.orglett.9b03095}
}
Cite this
MLA
Copy
Murray, Lauren A. M., et al. “Total Synthesis of Naphterpin and Marinone Natural Products.” Organic Letters, vol. 21, no. 20, Sep. 2019, pp. 8312-8315. https://doi.org/10.1021/acs.orglett.9b03095.