Organic Letters, volume 5, issue 17, pages 3155-3158
Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921
Janak Singh
1
,
David R Kronenthal
1
,
Mark Schwinden
1
,
Jollie D. Godfrey
1
,
Rita Fox
1
,
Edward J Vawter
1
,
Bo Zhang
1
,
Thomas P Kissick
1
,
Bharat Patel
1
,
Omar Mneimne
1
,
Michael Humora
1
,
Chris G Papaioannou
1
,
Walter Szymanski
1
,
Michael K.Y. Wong
1
,
Chien K Chen
1
,
James E Heikes
1
,
John D Dimarco
1
,
Jun Qiu
1
,
Rajendra P. Deshpande
1
,
Jack Z. Gougoutas
1
,
Richard H Mueller
1
1
Process Research and Development, The Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, New Jersey 08543, Process Research and Development, The Bristol-Myers Squibb Pharmaceutical Research Institute, 1 Squibb Drive, New Brunswick, New Jersey 08903, and Solid State Chemistry, The Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, New Jersey 08543
|
Publication type: Journal Article
Publication date: 2003-08-01
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
[reaction: see text] An efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921 was accomplished. Two short enantioselective syntheses of the common key intermediate (S)-alpha-aminoazepinone 6b were developed. Olefin 3 was converted to 6b via asymmetric hydrogenation. Alternatively, enyne 12 was converted to racemic alpha-aminoazepinone 15b, which was transformed to 6b by a practical dynamic resolution.
Top-30
Journals
|
1
2
3
|
|
|
Tetrahedron Letters
3 publications, 10%
|
|
|
European Journal of Organic Chemistry
2 publications, 6.67%
|
|
|
Chemical Reviews
2 publications, 6.67%
|
|
|
Synthesis
2 publications, 6.67%
|
|
|
Drug Metabolism and Disposition
1 publication, 3.33%
|
|
|
Acta Crystallographica Section E Structure Reports Online
1 publication, 3.33%
|
|
|
MolBank
1 publication, 3.33%
|
|
|
Coordination Chemistry Reviews
1 publication, 3.33%
|
|
|
ChemInform
1 publication, 3.33%
|
|
|
Chirality
1 publication, 3.33%
|
|
|
Chemistry - A European Journal
1 publication, 3.33%
|
|
|
Journal of Peptide Science
1 publication, 3.33%
|
|
|
Organic Process Research and Development
1 publication, 3.33%
|
|
|
Chemical Society Reviews
1 publication, 3.33%
|
|
|
Organic and Biomolecular Chemistry
1 publication, 3.33%
|
|
|
Organic Letters
1 publication, 3.33%
|
|
|
1
2
3
|
Publishers
|
1
2
3
4
5
6
7
|
|
|
Wiley
7 publications, 23.33%
|
|
|
Elsevier
4 publications, 13.33%
|
|
|
American Chemical Society (ACS)
4 publications, 13.33%
|
|
|
Royal Society of Chemistry (RSC)
2 publications, 6.67%
|
|
|
Georg Thieme Verlag KG
2 publications, 6.67%
|
|
|
American Society for Pharmacology and Experimental Therapeutics
1 publication, 3.33%
|
|
|
International Union of Crystallography (IUCr)
1 publication, 3.33%
|
|
|
MDPI
1 publication, 3.33%
|
|
|
1
2
3
4
5
6
7
|
- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Singh J. et al. Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921 // Organic Letters. 2003. Vol. 5. No. 17. pp. 3155-3158.
GOST all authors (up to 50)
Copy
Singh J., Kronenthal D. R., Schwinden M., Godfrey J. D., Fox R., Vawter E. J., Zhang B., Kissick T. P., Patel B., Mneimne O., Humora M., Papaioannou C. G., Szymanski W., Wong M. K., Chen C. K., Heikes J. E., Dimarco J. D., Qiu J., Deshpande R. P., Gougoutas J. Z., Mueller R. H. Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921 // Organic Letters. 2003. Vol. 5. No. 17. pp. 3155-3158.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ol0352308
UR - https://doi.org/10.1021/ol0352308
TI - Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921
T2 - Organic Letters
AU - Singh, Janak
AU - Kronenthal, David R
AU - Schwinden, Mark
AU - Godfrey, Jollie D.
AU - Fox, Rita
AU - Vawter, Edward J
AU - Kissick, Thomas P
AU - Patel, Bharat
AU - Mneimne, Omar
AU - Humora, Michael
AU - Papaioannou, Chris G
AU - Szymanski, Walter
AU - Wong, Michael K.Y.
AU - Chen, Chien K
AU - Heikes, James E
AU - Dimarco, John D
AU - Qiu, Jun
AU - Deshpande, Rajendra P.
AU - Gougoutas, Jack Z.
AU - Mueller, Richard H
AU - Zhang, Bo
PY - 2003
DA - 2003/08/01
PB - American Chemical Society (ACS)
SP - 3155-3158
IS - 17
VL - 5
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex
Copy
@article{2003_Singh,
author = {Janak Singh and David R Kronenthal and Mark Schwinden and Jollie D. Godfrey and Rita Fox and Edward J Vawter and Thomas P Kissick and Bharat Patel and Omar Mneimne and Michael Humora and Chris G Papaioannou and Walter Szymanski and Michael K.Y. Wong and Chien K Chen and James E Heikes and John D Dimarco and Jun Qiu and Rajendra P. Deshpande and Jack Z. Gougoutas and Richard H Mueller and Bo Zhang},
title = {Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921},
journal = {Organic Letters},
year = {2003},
volume = {5},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/ol0352308},
number = {17},
pages = {3155--3158},
doi = {10.1021/ol0352308}
}
Cite this
MLA
Copy
Singh, Janak, et al. “Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921.” Organic Letters, vol. 5, no. 17, Aug. 2003, pp. 3155-3158. https://doi.org/10.1021/ol0352308.