Synthesis and Anti-HIV Activity of Lupane and Olean-18-ene

FÁTIMA GUTIÉRREZ NICOLÁS; BÁRABARA GORDILLO ROMÁN; J. C. OBERTI; A. ESTÉVEZ-BRAUN; A. G. RAVELO; PEDRO JOSEPH NATHAN

JOURNAL OF NATURAL PRODUCTS

AMER CHEMICAL SOC

Lugar: Washington; Año: 2012 vol. 75 p. 669 - 676

0163-3864

Lupane triterpenoids 2 and 5−12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure−activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFTcalculated vibrational circular dichroism spectra. The CompareVOA 2 and 5−12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure−activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFTcalculated vibrational circular dichroism spectra. The CompareVOA 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure−activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFTcalculated vibrational circular dichroism spectra. The CompareVOA 3), and germanicol (4). They were tested for anti-HIV activity, and some structure−activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFTcalculated vibrational circular dichroism spectra. The CompareVOA −activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFTcalculated vibrational circular dichroism spectra. The CompareVOA S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFTcalculated vibrational circular dichroism spectra. The CompareVOA 8) was assessed by comparison of the observed and DFTcalculated vibrational circular dichroism spectra. The CompareVOAVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures 2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structuresS)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures