|
|||||
|
|
Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor |
|
| Authors: | Palimécio G Guerrero Jr Paulo R de OliveiraAdriano CM Baroni Francisco A MarquesRicardo Labes Gabriela R HurtadoMiguel J Dabdoub |
| Institution: | a Department of Chemistry and Biology, DAQBi, Paraná Federal University of Technology, UTFPR, Curitiba, PR, Brazil b Department of Pharmacy-Biochemistry, Federal University of Mato Grosso do Sul, UFMS, Campo Grande, MS, Brazil c Department of Chemistry, Federal University of Paraná, UFPR, Curitiba, PR, Brazil d Department of Chemistry, Federal University of Mato Grosso do Sul, UFMS, Campo Grande, MS, Brazil e Department of Chemistry, São Paulo State University, USP, Ribeirão Preto, SP, Brazil |
| Abstract: | An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the β-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. |
| Keywords: | Retinoid Temarotene Arotinoid acid (TTNPB) Synthesis (Z)-1 2-bis(organylchalcogene)-1-alkene Anticancer |
| 本文献已被 ScienceDirect 等数据库收录！ | |