title: Gold(I) as an artificial cyclase: short stereodivergent syntheses of (-)-epiglobulol and (-)-4β,7α- and (-)-4α,7α-aromadendranediols.
abstract: Three natural aromadendrane sesquiterpenes, (-)-epiglobulol, (-)-4β,7α-aromadendranediol, and (-)-4α,7α-aromadendranediol, have been synthesized in only seven steps in 12, 15, and 17 % overall yields, respectively, from (E,E)-farnesol by a stereodivergent gold(I)-catalyzed cascade reaction which forms the tricyclic aromadendrane core in a single step. These are the shortest total syntheses of these natural compounds.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain).
authors.forename: Javier
authors.initials: J
authors.lastname: Carreras
authors.forename: Madeleine
authors.initials: M
authors.lastname: Livendahl
authors.forename: Paul R
authors.initials: PR
authors.lastname: McGonigal
authors.forename: Antonio M
authors.initials: AM
authors.lastname: Echavarren
mesh_terms: D004798:Enzymes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D045789:Sesquiterpenes, Guaiane; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D004798:Enzymes; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C543650:aromadendranediol; D006046:Gold
keywords: cyclization; gold; natural products; terpenoids; total synthesis