volume 21 issue 20 pages 8312-8315

Total Synthesis of Naphterpin and Marinone Natural Products

Publication typeJournal Article
Publication date2019-09-24
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
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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GOST |
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GOST Copy
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) Copy
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.
RIS |
Cite this
RIS Copy
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 -
BibTex |
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}
}
MLA
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.