title: Facile access to optically active ring C aromatic diterpene derivatives from (+)-manool. first synthesis of 13,14-dihydroxy8,11,13-podocarpatrien-7-one.
abstract: 14,15,17-Trinorlabdan-8,13-dione 6 was efficiently synthesized via ozonolysis of(+)-manool (4) followed by treatment with aqueous NaOH in the presence of tetra-n-butylammonium bromide as catalyst. This protocol has the advantages of high yield, mild conditions and simple procedure. Utilizing this strategy, the first enantiospecific synthesis of 13,14-dihydroxy-8,11,13-podocarpatrien-7-one (1), a constituent of Taiwania cryptomerioides and Celastrus paniculatus, was achieved starting from (+)-manool (4) after a four-step sequence in 24% overall yield.
authors.forename: Maria L
authors.initials: ML
authors.lastname: Nóvoa
authors.forename: Franklin J
authors.initials: FJ
authors.lastname: Salazar
authors.forename: Carlos
authors.initials: C
authors.lastname: Gámez
authors.forename: Ana Y
authors.initials: AY
authors.lastname: Angarita
authors.forename: Eleonora
authors.initials: E
authors.lastname: Tropper
authors.forename: Nieves
authors.initials: N
authors.lastname: Canudas
authors.forename: José E
authors.initials: JE
authors.lastname: Villamizar
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C588198:13,14-dihydroxy-8,11,13-podocarpatrien-7-one; D004224:Diterpenes; C482828:manool