Tetrahedron, volume 124, pages 133016
Origin of the selectivity in the ring-closing metathesis step of the synthesis of (−)-callyspongiolide: Formation of fourteen-versus eight-membered rings
Publication type: Journal Article
Publication date: 2022-10-01
Journal:
Tetrahedron
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
In previous work we reported the formal synthesis of the marine macrolide (−)-callyspongiolide through a synthetic approach in which the generation of the key macrocyclic core relies on a ruthenium-catalyzed ring-closing metathesis reaction. However, besides the predicted macrolactone intermediate, an undesired cyclooctene was observed. We investigate here the mechanism of this critical step through density functional theory calculations. The results indicate that the chemoselectivity is not under kinetic control but ruled by thermodynamics. This conclusion is further confirmed by additional experimental studies.
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Russian Chemical Reviews
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 100%
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Díaz-Ruiz M. et al. Origin of the selectivity in the ring-closing metathesis step of the synthesis of (−)-callyspongiolide: Formation of fourteen-versus eight-membered rings // Tetrahedron. 2022. Vol. 124. p. 133016.
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Díaz-Ruiz M., Urbina A., Llor N., Bosch J., Amat M., Maseras F. Origin of the selectivity in the ring-closing metathesis step of the synthesis of (−)-callyspongiolide: Formation of fourteen-versus eight-membered rings // Tetrahedron. 2022. Vol. 124. p. 133016.
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TY - JOUR
DO - 10.1016/j.tet.2022.133016
UR - https://doi.org/10.1016/j.tet.2022.133016
TI - Origin of the selectivity in the ring-closing metathesis step of the synthesis of (−)-callyspongiolide: Formation of fourteen-versus eight-membered rings
T2 - Tetrahedron
AU - Díaz-Ruiz, Marina
AU - Urbina, A.
AU - Llor, Núria
AU - Bosch, Joan
AU - Amat, Mercedes
AU - Maseras, Feliu
PY - 2022
DA - 2022/10/01 00:00:00
PB - Elsevier
SP - 133016
VL - 124
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2022_Díaz-Ruiz,
author = {Marina Díaz-Ruiz and A. Urbina and Núria Llor and Joan Bosch and Mercedes Amat and Feliu Maseras},
title = {Origin of the selectivity in the ring-closing metathesis step of the synthesis of (−)-callyspongiolide: Formation of fourteen-versus eight-membered rings},
journal = {Tetrahedron},
year = {2022},
volume = {124},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/j.tet.2022.133016},
pages = {133016},
doi = {10.1016/j.tet.2022.133016}
}
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