title: "One-pot" reductive lactone alkylation provides a concise asymmetric synthesis of chiral isoprenoid targets.
abstract: An efficient method, based on nucleophilic addition to lactones followed by modified in situ Clemmensen reduction, provides a short synthetic route to chiral isoprenoid targets. The efficacy of this method has been exemplified through the synthesis of several targets including the commercial fragrance Rosaphen, the side chain of Zaragozic acid C, the cotton leaf sex pheromone, and the side chains of vitamin E.
authors: School of Chemistry, Monash University, Clayton VIC 3800, Australia.
authors: Jia
authors: J
authors: Cao
authors: Patrick
authors: P
authors: Perlmutter
mesh_terms: D000478:Alkylation; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; D013729:Terpenes; C079090:zaragozic acid C