Synthesis of branched carbasugars via photooxygenation and manganese(III) acetate free radical cyclization

Date

2014-08-19

Author

Altun, Yasemin
Dogan, Sengul Dilem
Balcı, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

181
views

0
downloads

Transformation of cyclohexa-1,3- and 1,4-dienes to carbasugars is described. Photooxygenation of dienes gave bicyclic endoperoxides, which were reduced with thiourea to the corresponding 1,4-dials with cis-configuration. Lactonization of the remaining double bond by oxidative addition of acetic acid to the double bond in the presence of Mn(OAc)(3) followed by lactone ring-opening reaction gave the target branched carbasugars.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/57458

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2014.05.069

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Coupling of cyclopropylcarbene-chromium complex with ferrocenyl alkynes: synthesis of 5-ferrocenyl-5-hydroxy-2-cyclopentenones and 4-ferrocenyl-4-cyclopentene-1,3-diones Zora, Metin; Bueyuekguengoer, Orhan (Elsevier BV, 2007-05-07) The coupling of ferrocenyl alkynes with cyclopropylcarbene-chromium complex leads to ferrocenyl-substituted 2-cyclopentenones with or without a hydroxy substituent, namely 4-cyclopentene-1,3-diones, 2-cyclobutenones, and alpha, beta-unsaturated aldehydes in varying amounts. The reaction initially produces a cyclopentadienone intermediate, then to the double bond of which, bearing a ferrocenyl group, addition of water occurs to afford hydroxy-substituted 2-cyclopentenones. In all the products, the hydroxy gr...
Synthesis of triazene-substituted homoconjugated push-pull chromophores by formal [2 + 2] cycloadditions Erden, Kübra; Dengiz, Çağatay (Elsevier BV, 2019-07-25) 1-(4-Ethynylphenyl)-3,3-dialkyltriaz-1-enes, well-known building blocks for branched dendrimer syntheses, were utilized as a new type of electron-donor component in formal [2 + 2] cycloadditions. The click-type, atom-economic reactions proceed efficiently under ambient conditions without any catalyst. The resulting products are structurally interesting push-pull chromophores and were investigated in the context of optoelectronic properties using UV/Vis spectroscopy, NMR studies, and computational chemistry
Synthesis of various camphor-based chiral pyridine derivatives Tanyeli, Cihangir; Isik, M (Elsevier BV, 2004-07-19) (+)-beta-Hydroxymethylenecamphor 1 and enamines 2a-e were transformed into chiral camphor-based pyridine derivatives 3a-e via a tandem condensation reaction in good yields.
Synthesis of ferrocenyl quinones Zora, Metin; Acikalin, S (Elsevier BV, 2003-03-03) A squarate-based synthesis of ferrocenyl quinones is described. Thermolysis of ferrocenyl-substituted cyclobutenones, prepared from ferrocenyl cyclobutenediones and alkenyllithiums, affords hydroquinones, which furnish, upon oxidation, ferrocenyl quinones. Ferrocenyl cyclobutenediones have been prepared from known cyclo butenediones by nucleophilic addition of ferrocenyllithium followed by hydrolysis, Pd/Cu-cocatalyzed cross-coupling with (tri-n-butylstannyl)ferrocene or Friedel-Crafts alkylation with ferro...
Reaction of ferrocenylcarbene complexes of Cr, Mo and W with alkynes: Synthesis of ferrocenylcyclobutenones, ferrocenylfurans and ferrocenylketoesters Zora, Metin (Elsevier BV, 2001-07-09) Ferrocenylcarbene complexes of Cr, Mo and W react with alkynes to produce cyclobutenones, furans and/or ketoesters. The reaction is quite sensitive to the substituents of the alkyne, regardless of the identity of the metal. Cyclobutenones are formed only in the reactions of diphenylacetylene, a rare occurrence for metal carbene complexes. Ketoesters are secondary reaction products and result From oxidation of furan derivatives during the course of the reaction and/or silica-gel chromatography.

Citation Formats

Y. Altun, S. D. Dogan, and M. Balcı, “Synthesis of branched carbasugars via photooxygenation and manganese(III) acetate free radical cyclization,” TETRAHEDRON, pp. 4884–4890, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57458.