title: A unified approach to the daucane and sphenolobane bicyclo[5.3.0]decane core: enantioselective total syntheses of daucene, daucenal, epoxydaucenal B, and 14-para-anisoyloxydauc-4,8-diene.
abstract: Access to the bicyclo[5.3.0]decane core found in the daucane and sphenolobane terpenoids via a key enone intermediate enables the enantioselective total syntheses of daucene, daucenal, epoxydaucenal B, and 14-para-anisoyloxydauc-4,8-diene. Central aspects include a catalytic asymmetric alkylation followed by a ring contraction and ring-closing metathesis to generate the five- and seven-membered rings, respectively.
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, 1200 E. California Blvd, MC 101-20, Pasadena, CA 91125 (USA), Fax: (+1) 626-395-8436.
authors.forename: Nathan B
authors.initials: NB
authors.lastname: Bennett
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D001688:Biological Products; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes
chemical_list: D000473:Alkanes; D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D013729:Terpenes; C533056:daucene; C012867:decane
keywords: allylic alkylation; asymmetric catalysis; natural products; terpenoids; total synthesis