General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers
Тип публикации: Journal Article
Дата публикации: 2020-03-06
SCImago Q1
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WOS Q1
БС1
SJR: 1.007
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
PubMed ID:
32141756
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
A general synthetic strategy for antirhine alkaloids was developed in this study. The cyanide-catalyzed imino-Stetter reaction of ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde afforded the corresponding indole-3-acetic acid derivative. Subsequent formation of the six-membered C ring followed by trans-selective installation of the two-carbon unit at C-15 provided rapid access to the key intermediate. Stereoselective installation of substituents at C-20 allowed the total syntheses of (±)-antirhine, (±)-18,19-dihydroantirhine, and their 20-epimers, all of the known natural products in the antirhine family.
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ГОСТ
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Bae C. et al. General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers // Organic Letters. 2020. Vol. 22. No. 6. pp. 2354-2358.
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Bae C., Park E., Cho C., Cheon C. H. General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers // Organic Letters. 2020. Vol. 22. No. 6. pp. 2354-2358.
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TY - JOUR
DO - 10.1021/acs.orglett.0c00544
UR - https://doi.org/10.1021/acs.orglett.0c00544
TI - General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers
T2 - Organic Letters
AU - Bae, Cheolwoo
AU - Park, Eunjoon
AU - Cho, Cheon-Gyu
AU - Cheon, Cheol Hong
PY - 2020
DA - 2020/03/06
PB - American Chemical Society (ACS)
SP - 2354-2358
IS - 6
VL - 22
PMID - 32141756
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (до 50 авторов)
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@article{2020_Bae,
author = {Cheolwoo Bae and Eunjoon Park and Cheon-Gyu Cho and Cheol Hong Cheon},
title = {General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.orglett.0c00544},
number = {6},
pages = {2354--2358},
doi = {10.1021/acs.orglett.0c00544}
}
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MLA
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Bae, Cheolwoo, et al. “General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers.” Organic Letters, vol. 22, no. 6, Mar. 2020, pp. 2354-2358. https://doi.org/10.1021/acs.orglett.0c00544.
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