- Potent antimalarial febrifugine analogues against the Plasmodium malaria parasite
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Although febrifugine (1) and isofebrifugine (2), alkaloids isolated from roots of the Dichroa febrifuga plant, show powerful antimalarial activity against Plasmodium falciparum, strong side effects such as the emetic effect have precluded their clinical u
- Kikuchi, Haruhisa,Tasaka, Hidehisa,Hirai, Shingo,Takaya, Yoshiaki,Iwabuchi, Yoshiharu,Ooi, Hidenori,Hatakeyama, Susumi,Kim, Hye-Sook,Wataya, Yusuke,Oshima, Yoshiteru
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p. 2563 - 2570
(2007/10/03)
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- Stereoselective Cyclization of 4-Substituted 5-Hexen-1-ols and Related Compounds by Benzeneselenenyl Triflate
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Oxyselenylation of 4-substituted 5-hexen-1-ols 1 with benzeneselenenyl trifluoromethanesulfonate proceeds by intramolecular exo cyclization stereoselectively to give 3-substituted trans- or cis-2-(phenylselenenylmethyl)tetrahydropyrans 3.Formation of the trans isomers is favored when the substituents contain alkyl or phenyl substituents in the 4-position, whereas the cis isomers predominate when the substituents are alkoxyalkyl, alkoxyl, acyl, and hydroxyl.The mechanism of the trans and cis stereoselectivity is explained by steric and electronic effects in the phenylseleniranium intermediates, 7 and 8. - Key Words: Oxyselenenylation / Benzeneselenenyl triflate / Selenium compounds / Trifluoromethanesulfonate / Alkenols
- Inoue, Hirohumi,Murata, Shizuaki,Suzuki, Toshiyasu
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p. 901 - 910
(2007/10/02)
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