Author/Authors :
Morokuma، نويسنده , , Kenji and Taira، نويسنده , , Yuko and Uehara، نويسنده , , Yumiko and Shibahara، نويسنده , , Setsuya and Takahashi، نويسنده , , Keisuke and Ishihara، نويسنده , , Jun and Hatakeyama، نويسنده , , Susumi، نويسنده ,
Abstract :
Aldol reaction of di-tert-butyl 4-(4-methoxybenzyloxy)-2-oxobutanoate with pent-4-enal using (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride as a catalyst, followed by Pinnick oxidation and tert-butyl esterification, gave (2S,3S)-di-tert-butyl 2-(2-(4-methoxybenzyloxy)ethyl)-3-allyl-2-hydroxysuccinate in high optical purity (85% ee), from which the total synthesis of (+)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished.
