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

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

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-diols with cis-configuration. Lactonization of the remaining double bond by oxidative addition of acetic acid...

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Veröffentlicht in:Tetrahedron 2014-08, Vol.70 (33), p.4884-4890
Hauptverfasser: Altun, Yasemin, Dogan, Sengul Dilem, Balci, Metin
Format: Artikel
Sprache:eng
Schlagworte:
Acetic acid
Bonding
Branched
Branched carbasugars
Carbasugars
Cyclitol
Free radicals
Lactones
Mn(OAc)3 oxidation
Photooxygenation
Synthesis (chemistry)
Tetrahedrons
Transformations
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Zusammenfassung: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-diols 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.05.069