RESUMEN
The first stereoselective total synthesis of gonytolide C, which is a monomeric unit of an innate immune promoter gonytolide A, has been accomplished from the aldol reaction between acetophenone derived from orcinol and butyrolactone containing α-keto ester followed by the excellent diastereoselective intramolecular cyclization. The first total synthesis of gonytolide G has been achieved by the oxidation of benzylic methyl in gonytolide C. Additionally, total synthesis of lachnone C and a formal synthesis of blennolide C and diversonol have been achieved by this synthetic method.
Asunto(s)
4-Butirolactona/análogos & derivados , Cromonas/síntesis química , Lactonas/síntesis química , Xantonas/síntesis química , 4-Butirolactona/síntesis química , 4-Butirolactona/química , Cromonas/química , Lactonas/química , Espectroscopía de Protones por Resonancia Magnética , Estereoisomerismo , Temperatura , Factores de Tiempo , Xantonas/químicaRESUMEN
A first total synthesis of acortatarins A, B, and an enantiomer of the proposed structure of acortatarin B is described by using readily available d-sugars. This convergent total synthesis revealed the revision of the absolute configuration of acortatarin A and structural revision of acortatarin B. The key steps involved are regioselective epoxide opening with deprotonated 2,5-disubstituted pyrrole and spiroketalization.