Regioselective Preparation of 2-Substituted 3,4-Diaryl Pyrroles: A Concise Total Synthesis of Ningalin B
Тип публикации: Journal Article
Дата публикации: 2002-12-01
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
12492350
Organic Chemistry
Краткое описание
Methylisocyanoacetate undergoes a 2 + 3 cycloaddition with alpha,beta-unsaturated nitriles to provide a regioselective synthesis of 2-substituted 3,4-diaryl pyrroles. The ease of preparation of alpha,beta-unsaturated nitriles allows the rapid synthesis of pyrroles with varied substituents. Using this method, a key intermediate (1) for the synthesis of the marine natural products lukianol A, lamellarin O, and lamellarin Q was prepared in two steps. A total synthesis of ningalin B (11) was also accomplished utilizing this methodology.
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Bullington J. L., Wolff R. R., Jackson P. F. Regioselective Preparation of 2-Substituted 3,4-Diaryl Pyrroles: A Concise Total Synthesis of Ningalin B // Journal of Organic Chemistry. 2002. Vol. 67. No. 26. pp. 9439-9442.
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Bullington J. L., Wolff R. R., Jackson P. F. Regioselective Preparation of 2-Substituted 3,4-Diaryl Pyrroles: A Concise Total Synthesis of Ningalin B // Journal of Organic Chemistry. 2002. Vol. 67. No. 26. pp. 9439-9442.
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TY - JOUR
DO - 10.1021/jo026445i
UR - https://doi.org/10.1021/jo026445i
TI - Regioselective Preparation of 2-Substituted 3,4-Diaryl Pyrroles: A Concise Total Synthesis of Ningalin B
T2 - Journal of Organic Chemistry
AU - Bullington, James L
AU - Wolff, Russell R
AU - Jackson, Paul F.
PY - 2002
DA - 2002/12/01
PB - American Chemical Society (ACS)
SP - 9439-9442
IS - 26
VL - 67
PMID - 12492350
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2002_Bullington,
author = {James L Bullington and Russell R Wolff and Paul F. Jackson},
title = {Regioselective Preparation of 2-Substituted 3,4-Diaryl Pyrroles: A Concise Total Synthesis of Ningalin B},
journal = {Journal of Organic Chemistry},
year = {2002},
volume = {67},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/jo026445i},
number = {26},
pages = {9439--9442},
doi = {10.1021/jo026445i}
}
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MLA
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Bullington, James L., et al. “Regioselective Preparation of 2-Substituted 3,4-Diaryl Pyrroles: A Concise Total Synthesis of Ningalin B.” Journal of Organic Chemistry, vol. 67, no. 26, Dec. 2002, pp. 9439-9442. https://doi.org/10.1021/jo026445i.