Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core
Kassrin Tangdenpaisal
1
,
Poramate Songthammawat
2
,
Kornkamon Akkarasereenon
2
,
Kanokpish Chuayboonsong
2
,
Somsak Ruchirawat
1, 2, 3
,
Poonsakdi Ploypradith
1, 2, 3
2
Program in Chemical Biology, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, 906 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand
|
3
Centre of Excellence on Environmental Health and Toxicology, Commission on Higher Education (CHE), Ministry of Education, Bangkok 10400, Thailand
|
Publication type: Journal Article
Publication date: 2019-08-14
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31409069
Organic Chemistry
Abstract
In four steps from the tricyclic core, palodesangren B trimethyl ether and palodesangren D dimethyl ether could be synthesized in 29 and 18% overall yields, respectively. A reaction sequence comprising the regioselective MgCl2-mediated Casnati-Skattebøl ortho-formylation of phenol, Wittig methylenation, acryloylation, and Ru(II)-catalyzed ring-closing metathesis (RCM) led to the formation of the final 2H-pyran-2-one ring of the desired tetracyclic core.
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Total citations:
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Citations from 2024:
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(33.33%)
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GOST
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Tangdenpaisal K. et al. Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core // Journal of Organic Chemistry. 2019. Vol. 84. No. 21. pp. 13410-13429.
GOST all authors (up to 50)
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Tangdenpaisal K., Songthammawat P., Akkarasereenon K., Chuayboonsong K., Ruchirawat S., Ploypradith P. Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core // Journal of Organic Chemistry. 2019. Vol. 84. No. 21. pp. 13410-13429.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.9b01596
UR - https://doi.org/10.1021/acs.joc.9b01596
TI - Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core
T2 - Journal of Organic Chemistry
AU - Tangdenpaisal, Kassrin
AU - Songthammawat, Poramate
AU - Akkarasereenon, Kornkamon
AU - Chuayboonsong, Kanokpish
AU - Ruchirawat, Somsak
AU - Ploypradith, Poonsakdi
PY - 2019
DA - 2019/08/14
PB - American Chemical Society (ACS)
SP - 13410-13429
IS - 21
VL - 84
PMID - 31409069
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Tangdenpaisal,
author = {Kassrin Tangdenpaisal and Poramate Songthammawat and Kornkamon Akkarasereenon and Kanokpish Chuayboonsong and Somsak Ruchirawat and Poonsakdi Ploypradith},
title = {Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.joc.9b01596},
number = {21},
pages = {13410--13429},
doi = {10.1021/acs.joc.9b01596}
}
Cite this
MLA
Copy
Tangdenpaisal, Kassrin, et al. “Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core.” Journal of Organic Chemistry, vol. 84, no. 21, Aug. 2019, pp. 13410-13429. https://doi.org/10.1021/acs.joc.9b01596.