103773-79-1Relevant articles and documents
Preparation of (2R,4S)/(2S,4S)-4-hydroxypipecolinic acid derivatives from L-(-)-malic acid
Yin, Shuqiang,Taneda, Hiroshi,Li, Bozhi,Zhou, Dejun,Minato, Daishiro,Sugimoto, Kenji,Matsuya, Yuji
, p. 928 - 938 (2015)
Synthetically important 4-hydroxypipecolinic acid derivatives were efficiently prepared from commercially available L-(-)-malic acid. The stereochemistries of the derivatives synthesized by our method were determined by coupling constant analyses with key methine protons on C2 and C4.
Transacetalization of acetals with butane-1,2,4-triol using cobalt(II) chloride and chlorotrimethylsilane
Battisti, Umberto Maria,Sorbi, Claudia,Franchini, Silvia,Tait, Annalisa,Brasili, Livio
, p. 943 - 946 (2014)
Transacetalization of acetals with butane-1,2,4-triol was carried out using cobalt(II) chloride and chlorotrimethylsilane as catalysts. The reaction occurs under mild conditions in acetonitrile and with a short reaction time. The synergic effect of the two Lewis acids catalyzes the conversion of butane-1,2,4-triol into (2-alkyl- or 2-aryl-1,3-dioxan-4-yl)methanol derivatives with high regiospecificity and diasteroselectivity. Georg Thieme Verlag Stuttgart · New York.
Total Synthesis and Biological Evaluation of Siladenoserinol A and its Analogues
Yoshida, Masahito,Saito, Koya,Kato, Hikaru,Tsukamoto, Sachiko,Doi, Takayuki
supporting information, p. 5147 - 5150 (2018/03/26)
The total synthesis of siladenoserinol A, an inhibitor of the p53–Hdm2 interaction, has been achieved. AuCl3-catalyzed hydroalkoxylation of an alkynoate derivative smoothly and regioselectively proceeded to afford a bicycloketal in excellent yield. A glycerophosphocholine moiety was successfully introduced through the Horner–Wadsworth–Emmons reaction using an originally developed phosphonoacetate derivative. Finally, removal of the acid-labile protecting groups, followed by regioselective sulfamate formation of the serinol moiety afforded the desired siladenoserinol A, and benzoyl and desulfamated analogues were also successfully synthesized. Biological evaluation showed that the sulfamate is essential for biological activity, and modification of the acyl group on the bicycloketal can improve the inhibitory activity against the p53–Hdm2 interaction.