Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids
Publication type: Journal Article
Publication date: 2009-03-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The conditions of the Eschenmoser coupling reaction were studied. The formation of the α-thioiminium ion was achieved faster in the presence of an additive (NaI) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives.
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59
Total citations:
59
Citations from 2025:
2
(3.39%)
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Neto B. A. D. et al. Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids // Tetrahedron. 2009. Vol. 65. No. 12. pp. 2484-2496.
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Neto B. A. D., Lapis A. A., Bernd A. B., Russowsky D. Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids // Tetrahedron. 2009. Vol. 65. No. 12. pp. 2484-2496.
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RIS
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TY - JOUR
DO - 10.1016/j.tet.2009.01.081
UR - https://doi.org/10.1016/j.tet.2009.01.081
TI - Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids
T2 - Tetrahedron
AU - Neto, Brenno A. D.
AU - Lapis, Alexandre A.M.
AU - Bernd, Alinne B
AU - Russowsky, Dennis
PY - 2009
DA - 2009/03/01
PB - Elsevier
SP - 2484-2496
IS - 12
VL - 65
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{2009_Neto,
author = {Brenno A. D. Neto and Alexandre A.M. Lapis and Alinne B Bernd and Dennis Russowsky},
title = {Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids},
journal = {Tetrahedron},
year = {2009},
volume = {65},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/j.tet.2009.01.081},
number = {12},
pages = {2484--2496},
doi = {10.1016/j.tet.2009.01.081}
}
Cite this
MLA
Copy
Neto, Brenno A. D., et al. “Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids.” Tetrahedron, vol. 65, no. 12, Mar. 2009, pp. 2484-2496. https://doi.org/10.1016/j.tet.2009.01.081.