RESUMEN
A variety of inositol phosphates including myo-inositol 1,4,5-trisphosphate, which is a secondary messenger in transmembrane signaling, were selectively synthesized via Yb(OTf)3-catalyzed desymmetrization of myo-inositol 1,3,5-orthoformate using a proline-based chiral anhydride as an acylation precursor. The investigated catalytic system could regioselectively differentiate the enantiotopic hydroxy groups of myo-inositol 1,3,5-orthoformate in the presence of a chiral auxiliary. This key step to generate a suitably protected chiral myo-inositol derivatives is described here as a unified approach to access inositol phosphates.
RESUMEN
An efficient chemical synthesis of mycothiol involving the regioselective ketopinyl desymmetrization of 2,4,5,6-tetrabenzylated D-myo-inositol as the key step is described. Together with a highly α-stereoselective D-glucosaminylation, the whole procedure was accomplished in eight steps with an overall yield of 40%.
Asunto(s)
Compuestos de Bencilo/química , Cisteína/síntesis química , Glicopéptidos/síntesis química , Inositol/análogos & derivados , Animales , Cisteína/química , Glicopéptidos/química , Inositol/síntesis química , Inositol/química , Fosfatos de Inositol/síntesis química , Estructura Molecular , EstereoisomerismoRESUMEN
A highly regioselective acylation of myo-inositol 1,3,5-orthoformate at the 4-O/6-O positions is catalyzed by various metal trifluoromethanesulfonates, giving excellent yields; an asymmetric example using (-)-camphanic anhydride is described here.