304665-09-6Relevant articles and documents
Stereoselective total synthesis of all the stereoisomers of (+)- and (?)-febrifugine and halofuginone
Perali, Ramu Sridhar,Bandi, Anjaneyulu
, (2020/07/04)
A convenient method for the total synthesis of all the stereoisomers of febrifugine and halofuginone using D-arabinose and L-arabinose as the key starting materials is reported. Apart from the inherent stereocenters in these pentose sugars, the method utilizes the selective hydrogenolysis of the anomeric O-benzyl group, stereoselective Grignard reaction and Wacker oxidation as the key steps to obtain the important precursors for the total synthesis.
Asymmetric synthesis of antimalarial alkaloids (+)-febrifugine and (+)-isofebrifugine
Huang, Pei-Qiang,Wei, Bang-Guo,Ruan, Yuan-Ping
, p. 1663 - 1667 (2007/10/03)
Diastereoselective α,-amidoalkylation of N,O-acetal, derivated from controlled regio and diastereoselective reduction of (S)-N-(4-methoxybenzyl)-3-silyloxyglutarimide provided two diastereomeric 6-allyl-5-silyloxy-2-piperidinones in 76:24 selectivity. The transformation of the major diastereomer into a known advanced intermediate allowed the synthesis of (+)-febrifugine and (+)-isofebrifugine.
