Total Synthesis of (−)-Pseudolaric Acid B
Publication type: Journal Article
Publication date: 2008-11-08
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
18998641
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
We report the enantioselective synthesis of pseudolaric acid B (1a), a diterpene acid isolated from the bark of Pseudolarix kaempferi Gordon, which displays interesting antifungal, antifertility, and cytotoxic activity against multidrug resistant cell lines. Our synthesis utilizes a highly efficient metal-catalyzed [5 + 2] vinylcyclopropane-alkyne intramolecular cycloaddition to construct the polyhydroazulene core of the natural product. Elaboration to the tricyclic scaffold of the pseudolaric acids was completed with an intramolecular alkoxycarbonyl radical cyclization to form the quaternary center and a highly diastereoselective cerium acetylide addition to a methyl ketone for introduction of the acid side chain.
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Metrics
112
Total citations:
112
Citations from 2024:
11
(9.82%)
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MLA
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GOST
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Trost B. M., Waser J., MEYER A. Total Synthesis of (−)-Pseudolaric Acid B // Journal of the American Chemical Society. 2008. Vol. 130. No. 48. pp. 16424-16434.
GOST all authors (up to 50)
Copy
Trost B. M., Waser J., MEYER A. Total Synthesis of (−)-Pseudolaric Acid B // Journal of the American Chemical Society. 2008. Vol. 130. No. 48. pp. 16424-16434.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ja806724x
UR - https://doi.org/10.1021/ja806724x
TI - Total Synthesis of (−)-Pseudolaric Acid B
T2 - Journal of the American Chemical Society
AU - Trost, Barry M.
AU - Waser, Jerome
AU - MEYER, ARNDT
PY - 2008
DA - 2008/11/08
PB - American Chemical Society (ACS)
SP - 16424-16434
IS - 48
VL - 130
PMID - 18998641
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2008_Trost,
author = {Barry M. Trost and Jerome Waser and ARNDT MEYER},
title = {Total Synthesis of (−)-Pseudolaric Acid B},
journal = {Journal of the American Chemical Society},
year = {2008},
volume = {130},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/ja806724x},
number = {48},
pages = {16424--16434},
doi = {10.1021/ja806724x}
}
Cite this
MLA
Copy
Trost, Barry M., et al. “Total Synthesis of (−)-Pseudolaric Acid B.” Journal of the American Chemical Society, vol. 130, no. 48, Nov. 2008, pp. 16424-16434. https://doi.org/10.1021/ja806724x.