title: Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD.
abstract: 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 DFT-calculated vibrational circular dichroism spectra. The CompareVOA 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.
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González, Departamento de Química Orgánica, Universidad de La Laguna, La Laguna 38206 Tenerife, Spain.
authors.forename: Fátima
authors.initials: F
authors.lastname: Gutiérrez-Nicolás
authors.forename: Bárbara
authors.initials: B
authors.lastname: Gordillo-Román
authors.forename: Juan C
authors.initials: JC
authors.lastname: Oberti
authors.forename: Ana
authors.initials: A
authors.lastname: Estévez-Braun
authors.forename: Angel G
authors.initials: AG
authors.lastname: Ravelo
authors.forename: Pedro
authors.initials: P
authors.lastname: Joseph-Nathan
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D019380:Anti-HIV Agents; D014315:Triterpenes