Rapid and diverse route to natural product-like biaryl ether containing macrocycles
Тип публикации: Journal Article
Дата публикации: 2003-09-12
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
A two-step sequence involving an Ugi four-component reaction and an intramol. nucleophilic arom. substitution (SNAr) has been developed for the rapid access to biaryl-ether contg. macrocycles. For example, reacting heptanal with butylamine, (3-hydroxyphenyl)acetic acid, and isonitrile I in dry toluene in the presence of NH4Cl gave dipeptide II. II was then cyclized using an intramol. SNAr sequence to give cyclic ether III as a mixt. of 4 diastereomers. In the course of this study, we documented that ammonium chloride can promote the Ugi-4CR in non-polar aprotic solvent (toluene) without the interference of an alternative Passerini reaction. Solid phase synthesis of macrocycles by this two-step sequence was also developed using polymer (Wang resin) supported alpha -(4'-fluoro-3'-nitro)phenethyl isocyanoacetate as one of the inputs. [on SciFinder (R)]
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Cristau P., Vors J., Zhu J. Rapid and diverse route to natural product-like biaryl ether containing macrocycles // Tetrahedron. 2003. Vol. 59. No. 40. pp. 7859-7870.
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Cristau P., Vors J., Zhu J. Rapid and diverse route to natural product-like biaryl ether containing macrocycles // Tetrahedron. 2003. Vol. 59. No. 40. pp. 7859-7870.
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TY - JOUR
DO - 10.1016/j.tet.2003.08.031
UR - https://doi.org/10.1016/j.tet.2003.08.031
TI - Rapid and diverse route to natural product-like biaryl ether containing macrocycles
T2 - Tetrahedron
AU - Cristau, Pierre
AU - Vors, Jean-Pierre
AU - Zhu, Jieping
PY - 2003
DA - 2003/09/12
PB - Elsevier
SP - 7859-7870
IS - 40
VL - 59
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2003_Cristau,
author = {Pierre Cristau and Jean-Pierre Vors and Jieping Zhu},
title = {Rapid and diverse route to natural product-like biaryl ether containing macrocycles},
journal = {Tetrahedron},
year = {2003},
volume = {59},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.tet.2003.08.031},
number = {40},
pages = {7859--7870},
doi = {10.1016/j.tet.2003.08.031}
}
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MLA
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Cristau, Pierre, et al. “Rapid and diverse route to natural product-like biaryl ether containing macrocycles.” Tetrahedron, vol. 59, no. 40, Sep. 2003, pp. 7859-7870. https://doi.org/10.1016/j.tet.2003.08.031.