Synthesis of arotinoid acid and temarotene using mixed (Z)-1, 2-bis (organylchalcogene)-1-alkene as precursor

…, PR de Oliveira, ACM Baroni, FA Marques, R Labes…

Index: Guerrero Jr., Palimecio G.; De Oliveira, Paulo R.; Baroni, Adriano C.M.; Marques, Francisco A.; Labes, Ricardo; Hurtado, Gabriela R.; Dabdoub, Miguel J. Tetrahedron Letters, 2012 , vol. 53, # 39 p. 5302 - 5305

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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 ...