title: Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B.
abstract: Starting from commercially available (+)-sclareolide, the first synthesis of zerumin B was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to an aldehyde intermediate and silyloxyfuran oxyfunctionalization as key steps. The synthesis established the relative and absolute configuration of zerumin B along with its identity with a purportedly new diterpenoid isolated from the plant Renealmia alpinia.
authors.affiliation: Département de Chimie, Université Laval, Quebec City, Quebec G1K 7P4, Canada. john.boukouvalas@chm.ulaval.ca
authors.forename: John
authors.initials: J
authors.lastname: Boukouvalas
authors.forename: Jian-Xin
authors.initials: JX
authors.lastname: Wang
authors.forename: Olivier
authors.initials: O
authors.lastname: Marion
authors.forename: Bruno
authors.initials: B
authors.lastname: Ndzi
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D030521:Zingiberaceae / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000970:Antineoplastic Agents; D004224:Diterpenes; D007783:Lactones; D013729:Terpenes; C520384:zerumin B