Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid.
Publication type: Journal Article
Publication date: 2015-06-18
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
26088188
General Chemistry
Catalysis
Abstract
A new strategy for highly concise, convergent, and enantioselective access to polydeoxypropionates has been developed. ZACA-Pd-catalyzed vinylation was used to prepare smaller deoxypropionate fragments, and then two key sequential Cu-catalyzed stereocontrolled sp(3)-sp(3) cross-coupling reactions allowed convergent assembly of smaller building blocks to build-up long polydeoxypropionate chains with excellent stereoselectivity. We employed this strategy for the synthesis of phthioceranic acid, a key constituent of the cell-wall lipid of Mycobacterium tuberculosis, in just 8 longest linear steps with full stereocontrol.
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Total citations:
30
Citations from 2025:
1
(3.33%)
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MLA
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GOST
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Xu S. et al. Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid. // Angewandte Chemie - International Edition. 2015. Vol. 54. No. 32. pp. 9319-9322.
GOST all authors (up to 50)
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Xu S., Oda A., Bobinski T., LI H., Matsueda Y., Negishi E. Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid. // Angewandte Chemie - International Edition. 2015. Vol. 54. No. 32. pp. 9319-9322.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/anie.201503818
UR - https://doi.org/10.1002/anie.201503818
TI - Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid.
T2 - Angewandte Chemie - International Edition
AU - Xu, Shiqing
AU - Oda, Akimichi
AU - Bobinski, Thomas
AU - LI, HAIJUN
AU - Matsueda, Yohei
AU - Negishi, Ei-ichi
PY - 2015
DA - 2015/06/18
PB - Wiley
SP - 9319-9322
IS - 32
VL - 54
PMID - 26088188
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2015_Xu,
author = {Shiqing Xu and Akimichi Oda and Thomas Bobinski and HAIJUN LI and Yohei Matsueda and Ei-ichi Negishi},
title = {Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid.},
journal = {Angewandte Chemie - International Edition},
year = {2015},
volume = {54},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/anie.201503818},
number = {32},
pages = {9319--9322},
doi = {10.1002/anie.201503818}
}
Cite this
MLA
Copy
Xu, Shiqing, et al. “Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid..” Angewandte Chemie - International Edition, vol. 54, no. 32, Jun. 2015, pp. 9319-9322. https://doi.org/10.1002/anie.201503818.