879899-01-1Relevant academic research and scientific papers
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.
Synthesis of (+)-febrifugine and a formal synthesis of (+)-halofuginone employing an organocatalytic direct vinylogous aldol reaction
Pansare, Sunil V.,Paul, Eldho K.
, p. 1863 - 1869 (2013/07/26)
The enantioselective organocatalytic direct vinylogous aldol reaction of γ-crotonolactone and a suitable aldehyde was utilized in the synthesis of a functionalized γ-butenolide. The γ-butenolide (aldol product) was stereoselectively converted into a 5-aminoalkyl butyrolactone, which isomerized to the key 2,3-disubstituted piperidinone, a common intermediate to (+)-febrifugine and (+)-halofuginone. Georg Thieme Verlag Stuttgart · New York.
Dihydroxylation of vinyl sulfones: Stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone
McLaughlin, Noel P.,Evans, Paul
supporting information; experimental part, p. 518 - 521 (2010/03/30)
(Chemical Equation Presented) The asymmetric dihydroxylation of amino-functionalized vinyl sulfone 19 has been used for the 3-step preparation of 3-hydroxylpiperidine 24 in 86% enantiomeric excess. This enantiomerically enriched building block was used then to synthesize the naturally occurring antimalarial alkaloid febrifugine 1 and its antiangiogenic analogue, halofuginone 3.
Chiral synthesis of (+)-febrifugine and (-)-isofebrifugine by means of samarium diiodide-promoted carbon-nitrogen bond cleavage reaction
Katoh, Miho,Matsune, Ryuichiro,Honda, Toshio
, p. 189 - 204 (2007/10/03)
(+)-Febrifugine, a potential anti-malarial piperidine alkaloid, was synthesized from (4S)-hydroxyproline methyl ester, stereoselectively, where a samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was involved as a key reaction. A stereocon
Stereocontrolled synthesis of a potent antimalarial alkaloid, (+)-febrifugine
Katoh, Miho,Matsune, Ryuichiro,Nagase, Hiromasa,Honda, Toshio
, p. 6221 - 6223 (2007/10/03)
A novel and stereocontrolled synthetic path to a potential antimalarial piperidine alkaloid, (+)-febrifugine, was established by employing a reductive deamination of a proline derivative with samarium diiodide, as a key step. A novel and stereocontrolled
