Stereoselective Syntheses of Highly Functionalized Bicyclo[3.1.0]hexanes: A General Methodology for the Synthesis of Potent and Selective mGluR2/3 Agonists
Lushi Tan
1
,
Nobuyoshi Yasuda
1
,
Naoki YOSHIKAWA
1
,
Frederick W. Hartner
1
,
Kan Kaung Eng
1
,
William R. Leonard
1
,
Fuh Rong Tsay
1
,
Ralph P. Volante
1
,
Richard D. Tillyer
1
1
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065
|
Тип публикации: Journal Article
Дата публикации: 2005-08-31
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
16277324
Organic Chemistry
Краткое описание
[Chemical reaction: See text] A Et3Al mediated intramolecular epoxide opening, cyclopropanation reaction is described. The transformation provided highly functionalized bicyclo[3.1.0]hexane systems in high efficiency and with perfect H or F endo selectivity. Application of this reaction to the synthesis of mGluR2/3 agonist 1 (43% overall yield) and a few intermediates suitable for the synthesis of other bicyclo[3.1.0]hexane mGluR2/3 agonists is discussed.
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Tan L. et al. Stereoselective Syntheses of Highly Functionalized Bicyclo[3.1.0]hexanes: A General Methodology for the Synthesis of Potent and Selective mGluR2/3 Agonists // Journal of Organic Chemistry. 2005. Vol. 70. No. 20. pp. 8027-8034.
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Tan L., Yasuda N., YOSHIKAWA N., Hartner F. W., Eng K. K., Leonard W. R., Tsay F. R., Volante R. P., Tillyer R. D. Stereoselective Syntheses of Highly Functionalized Bicyclo[3.1.0]hexanes: A General Methodology for the Synthesis of Potent and Selective mGluR2/3 Agonists // Journal of Organic Chemistry. 2005. Vol. 70. No. 20. pp. 8027-8034.
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TY - JOUR
DO - 10.1021/jo0511187
UR - https://doi.org/10.1021/jo0511187
TI - Stereoselective Syntheses of Highly Functionalized Bicyclo[3.1.0]hexanes: A General Methodology for the Synthesis of Potent and Selective mGluR2/3 Agonists
T2 - Journal of Organic Chemistry
AU - Tan, Lushi
AU - Yasuda, Nobuyoshi
AU - YOSHIKAWA, Naoki
AU - Hartner, Frederick W.
AU - Eng, Kan Kaung
AU - Leonard, William R.
AU - Tsay, Fuh Rong
AU - Volante, Ralph P.
AU - Tillyer, Richard D.
PY - 2005
DA - 2005/08/31
PB - American Chemical Society (ACS)
SP - 8027-8034
IS - 20
VL - 70
PMID - 16277324
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2005_Tan,
author = {Lushi Tan and Nobuyoshi Yasuda and Naoki YOSHIKAWA and Frederick W. Hartner and Kan Kaung Eng and William R. Leonard and Fuh Rong Tsay and Ralph P. Volante and Richard D. Tillyer},
title = {Stereoselective Syntheses of Highly Functionalized Bicyclo[3.1.0]hexanes: A General Methodology for the Synthesis of Potent and Selective mGluR2/3 Agonists},
journal = {Journal of Organic Chemistry},
year = {2005},
volume = {70},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/jo0511187},
number = {20},
pages = {8027--8034},
doi = {10.1021/jo0511187}
}
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Tan, Lushi, et al. “Stereoselective Syntheses of Highly Functionalized Bicyclo[3.1.0]hexanes: A General Methodology for the Synthesis of Potent and Selective mGluR2/3 Agonists.” Journal of Organic Chemistry, vol. 70, no. 20, Aug. 2005, pp. 8027-8034. https://doi.org/10.1021/jo0511187.