Journal of Organic Chemistry, volume 87, issue 2, pages 1313-1324
Enantiospecific Total Synthesis and Absolute Configuration Assignment of Chabrolobenzoquinone H
Publication type: Journal Article
Publication date: 2021-12-22
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Chabrolobenzoquinone H (1), a meroditerpene metabolite with cytotoxic activity, is synthesized via a stereoselective Julia-Kocienski olefination between a chiral pool derived aliphatic PT-sulfone and a benzoquinone aldehyde partner. The latter was obtained via consecutive chain extension steps involving a Stille coupling and a stereospecific olefin cross-metathesis reaction followed by malonic ester synthesis and a Krapcho decarboxylation. Furthermore, this total synthesis securely determined the absolute configuration of the targeted natural product.
Top-30
Citations by journals
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European Journal of Organic Chemistry
1 publication, 50%
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Russian Chemical Reviews
1 publication, 50%
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Citations by publishers
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Wiley
1 publication, 50%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 50%
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Rizos S. R., Ouzounthanasis K. A., Koumbis A. E. Enantiospecific Total Synthesis and Absolute Configuration Assignment of Chabrolobenzoquinone H // Journal of Organic Chemistry. 2021. Vol. 87. No. 2. pp. 1313-1324.
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Rizos S. R., Ouzounthanasis K. A., Koumbis A. E. Enantiospecific Total Synthesis and Absolute Configuration Assignment of Chabrolobenzoquinone H // Journal of Organic Chemistry. 2021. Vol. 87. No. 2. pp. 1313-1324.
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TY - JOUR
DO - 10.1021/acs.joc.1c02634
UR - https://doi.org/10.1021/acs.joc.1c02634
TI - Enantiospecific Total Synthesis and Absolute Configuration Assignment of Chabrolobenzoquinone H
T2 - Journal of Organic Chemistry
AU - Rizos, Stergios R
AU - Ouzounthanasis, Konstantinos A
AU - Koumbis, Alexandros E.
PY - 2021
DA - 2021/12/22 00:00:00
PB - American Chemical Society (ACS)
SP - 1313-1324
IS - 2
VL - 87
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2021_Rizos,
author = {Stergios R Rizos and Konstantinos A Ouzounthanasis and Alexandros E. Koumbis},
title = {Enantiospecific Total Synthesis and Absolute Configuration Assignment of Chabrolobenzoquinone H},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.joc.1c02634},
number = {2},
pages = {1313--1324},
doi = {10.1021/acs.joc.1c02634}
}
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MLA
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Rizos, Stergios R., et al. “Enantiospecific Total Synthesis and Absolute Configuration Assignment of Chabrolobenzoquinone H.” Journal of Organic Chemistry, vol. 87, no. 2, Dec. 2021, pp. 1313-1324. https://doi.org/10.1021/acs.joc.1c02634.