Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core
Publication type: Journal Article
Publication date: 2015-06-22
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
26084356
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
We report herein a facile and efficient method of the construction of the cis-1,2-oxazadecaline system, distinctive of (pre)trichodermamides, aspergillazine A, gliovirin, and FA-2097. The formation of the 1,2-oxazadecaline core was accomplished by a 1,2-addition of an αC-lithiated O-silyl ethyl pyruvate oxime to benzoquinone, which is followed by an oxa-Michael ring-closure. The method was successfully applied to the concise total synthesis of trichodermamide A (in gram quantities) and trichodermamide B, as well as the first synthesis of trichodermamide C.
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Metrics
33
Total citations:
33
Citations from 2024:
6
(18.18%)
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GOST
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Mfuh A. M. et al. Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core // Journal of the American Chemical Society. 2015. Vol. 137. No. 25. pp. 8050-8053.
GOST all authors (up to 50)
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Mfuh A. M., Zhang Yu., Stephens D. E., Vo A. X. T., Arman H. D., Larionov O. V. Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core // Journal of the American Chemical Society. 2015. Vol. 137. No. 25. pp. 8050-8053.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jacs.5b05205
UR - https://doi.org/10.1021/jacs.5b05205
TI - Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core
T2 - Journal of the American Chemical Society
AU - Mfuh, Adelphe M
AU - Zhang, Yu
AU - Stephens, David E
AU - Vo, Anh X T
AU - Arman, Hadi D.
AU - Larionov, Oleg V.
PY - 2015
DA - 2015/06/22
PB - American Chemical Society (ACS)
SP - 8050-8053
IS - 25
VL - 137
PMID - 26084356
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2015_Mfuh,
author = {Adelphe M Mfuh and Yu Zhang and David E Stephens and Anh X T Vo and Hadi D. Arman and Oleg V. Larionov},
title = {Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core},
journal = {Journal of the American Chemical Society},
year = {2015},
volume = {137},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/jacs.5b05205},
number = {25},
pages = {8050--8053},
doi = {10.1021/jacs.5b05205}
}
Cite this
MLA
Copy
Mfuh, Adelphe M., et al. “Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core.” Journal of the American Chemical Society, vol. 137, no. 25, Jun. 2015, pp. 8050-8053. https://doi.org/10.1021/jacs.5b05205.