Synthesis of the Parent and Substituted Tetracyclic ABCD Ring Cores of Camptothecins via 1-(3-Aryl-2-propynyl)- 1,6-dihydro-6-oxo-2-pyridinecarbonitriles
Тип публикации: Journal Article
Дата публикации: 2006-09-01
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
PubMed ID:
16986976
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
A new synthetic pathway to the parent and substituted ABCD ring cores of the camptothecin family of alkaloids was developed. The N-alkylation of 1,6-dihydro-6-oxo-2-pyridinecarbonitrile (2) with 3-bromo-1-phenylpropyne provided 3a using Curran's protocol. Treatment of 3a with a catalytic amount of DBU (5 mol %) at 110 degrees C for 12 h produced indolizino[1,2-b]quinolin-9(11H)-one (6a), the parent ABCD ring core of camptothecin, in essentially quantitative yield.
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Dai W., Petersen J. L., Wang K. Synthesis of the Parent and Substituted Tetracyclic ABCD Ring Cores of Camptothecins via 1-(3-Aryl-2-propynyl)- 1,6-dihydro-6-oxo-2-pyridinecarbonitriles // Organic Letters. 2006. Vol. 8. No. 20. pp. 4665-4667.
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Dai W., Petersen J. L., Wang K. Synthesis of the Parent and Substituted Tetracyclic ABCD Ring Cores of Camptothecins via 1-(3-Aryl-2-propynyl)- 1,6-dihydro-6-oxo-2-pyridinecarbonitriles // Organic Letters. 2006. Vol. 8. No. 20. pp. 4665-4667.
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TY - JOUR
DO - 10.1021/ol0620242
UR - https://doi.org/10.1021/ol0620242
TI - Synthesis of the Parent and Substituted Tetracyclic ABCD Ring Cores of Camptothecins via 1-(3-Aryl-2-propynyl)- 1,6-dihydro-6-oxo-2-pyridinecarbonitriles
T2 - Organic Letters
AU - Dai, Weixiang
AU - Petersen, Jeffrey L.
AU - Wang, Kung
PY - 2006
DA - 2006/09/01
PB - American Chemical Society (ACS)
SP - 4665-4667
IS - 20
VL - 8
PMID - 16986976
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2006_Dai,
author = {Weixiang Dai and Jeffrey L. Petersen and Kung Wang},
title = {Synthesis of the Parent and Substituted Tetracyclic ABCD Ring Cores of Camptothecins via 1-(3-Aryl-2-propynyl)- 1,6-dihydro-6-oxo-2-pyridinecarbonitriles},
journal = {Organic Letters},
year = {2006},
volume = {8},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/ol0620242},
number = {20},
pages = {4665--4667},
doi = {10.1021/ol0620242}
}
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MLA
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Dai, Weixiang, et al. “Synthesis of the Parent and Substituted Tetracyclic ABCD Ring Cores of Camptothecins via 1-(3-Aryl-2-propynyl)- 1,6-dihydro-6-oxo-2-pyridinecarbonitriles.” Organic Letters, vol. 8, no. 20, Sep. 2006, pp. 4665-4667. https://doi.org/10.1021/ol0620242.