title: Directed hydrogenation of acyclic homoallylic alcohols: enantioselective syntheses of (+)- and (-)-laurenditerpenol.
abstract: Laurenditerpenol is the first marine natural product shown to inhibit hypoxia-inducible factor 1 (HIF-1) activation. Preclinical studies support that the inhibition of HIF-1 is one of the molecular targets for antitumor drug discovery. The synthetically challenging molecular architecture of laurenditerpenol, its absolute stereostructure, and the biological activity of several diastereoisomers were accomplished by our group in 2007 by diastereoselective synthesis. Herein, we report enantioselective syntheses of both enantiomers of laurenditerpenol involving sequential Michael addition and remote homoallylic hydroxyl group-directed asymmetric hydrogenation at ambient temperature and pressure as key reaction steps. The current approach is elegant and overall more efficient than the ones previously reported in the literature.
authors.affiliation: National Center for Natural Products Research, ‡Department of Medicinal Chemistry, and §Department of Pharmacognosy, School of Pharmacy, University of Mississippi , University, Mississippi 38677, United States.
authors.forename: Amar G
authors.initials: AG
authors.lastname: Chittiboyina
authors.forename: Prabhakar
authors.initials: P
authors.lastname: Peddikotla
authors.forename: Mitchell A
authors.initials: MA
authors.lastname: Avery
authors.forename: Ikhlas A
authors.initials: IA
authors.lastname: Khan
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D020005:Propanols; C496938:laurenditerpenol; C006463:allyl alcohol