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Stereoselective Synthesis of Oxazolidin-2-Ones via an Asymmetric Aldol/Curtius Reaction: Concise Total Synthesis of (−)-Cytoxazone

Autor: Joohee Choi, Hanho Jang, Hosam Choi, Kiyoun Lee

Publikováno v: Molecules, Vol 26, Iss 597, p 597 (2021)
Molecules
Volume 26
Issue 3

Herein, we are reporting an efficient approach toward the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds. The developed approach is based on a combination of an asymmetric aldol and a modified Curtius protocol, which uses an effective intr

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::79bf6504f08a67f673455a5ce38541c8
https://www.mdpi.com/1420-3049/26/3/597

Synthesis Approaches to (−)-Cytoxazone, a Novel Cytokine Modulator, and Related Structures

Autor: Izabel L. Miranda, Ítala K. B. Lopes, Marisa A. N. Diaz, Gaspar Diaz

Publikováno v: Molecules, Vol 21, Iss 9, p 1176 (2016)

(−)-Cytoxazone, originally isolated from cultures of a Streptomyces species has an oxazolidin-2-one 4,5-disubstituted ring. It is known that this natural product presents a cytokine modulator effect through the signaling pathway of Th2 cells (type

Externí odkaz: https://doaj.org/article/3deaf505e42f41da816b0462e944f011

Concise synthesis of the Taxol side chain and demethoxy-4-epi-cytoxazone via oxazoline formation through intramolecular benzylic substitution of a bis-trichloroacetimidate

Autor: Mina Orita, Yoshitaka Matsushima

Publikováno v: Tetrahedron Letters. 73:153095

A concise and efficient method for synthesizing the Taxol side chain via the corresponding oxazoline intermediate was developed. The oxazoline ring is formed via an SN1 mechanism to ensure that the trans-oxazoline stereochemistry is retained. This pr

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::bacea3e079722db2cf6756ee4cf4b2c6
https://doi.org/10.1016/j.tetlet.2021.153095

New Approach for the Stereoselective Synthesis of (+)-epi-Cytoxazone

Autor: Gaspar Diaz-Muñoz, Marisa Alves Nogueira Diaz, Izabel Luzia Miranda, Suélen K. Sartori

Publikováno v: Journal of the Brazilian Chemical Society, Volume: 30, Issue: 3, Pages: 585-591, Published: MAR 2019
Journal of the Brazilian Chemical Society v.30 n.3 2019
Journal of the Brazilian Chemical Society
Sociedade Brasileira de Química (SBQ)
instacron:SBQ

The stereoselective total synthesis of (+)-epi-cytoxazone was performed satisfactorily in 8 steps, in 17% overall yield, via a novel route from 2,3-O-(3-pentylidene)-(R)-glyceraldehyde. The bulky group alkene-ketal allowed intramolecular control of t

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5a3e04fea41342ed04b33607e7ef64ef
https://doi.org/10.21577/0103-5053.20180212