title: A new route toward 7-Oxo-13-hydroxy-8,11,13-podocarpatrienes from labdane diterpenes.
abstract: Trinorlabdane 1,5-diketones (7, 10a,b, 13a,b), which are easily prepared from labdane diterpenes, are directly converted into the corresponding 7-oxo-13-hydroxy-8,11,13-podocarpatrienes, immediate precursors of bioactive compounds, under basic treatment. Utilizing this strategy, the first enantiospecific synthesis of 13-hydroxy-8,11,13-podocarpatriene (20), a constituent of Taiwania cryptomerioides, was achieved starting from (-)-sclareol (5) after a seven-step sequence in 55% overall yield.
authors.affiliation: Departamento de Química Organica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, Spain. eamr@ugr.es
authors.forename: Enrique
authors.initials: E
authors.lastname: Alvarez-Manzaneda Roldán
authors.forename: Juan Luis
authors.initials: JL
authors.lastname: Romera Santiago
authors.forename: Rachid
authors.initials: R
authors.lastname: Chahboun
mesh_terms: D045784:Abietanes / Q000737:chemistry* / Q000145:classification; D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000145:classification; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry
chemical_list: D045784:Abietanes; D004224:Diterpenes; D007659:Ketones