title: Prediction of a new pathway to presilphiperfolanol.
abstract: Quantum chemical calculations on the conversion of farnesyl diphosphate to presilphiperfolanol are described. On the basis of the results of this theoretical study, we predict a new mechanism for presilphiperfolanol formation that involves the intermediacy of nerolidyl diphosphate and an unusual reaction step in which a 1,2-alkyl shift and a transannular alkene attack are combined into a concerted process.
authors.affiliation: University of California-Davis, 1 Shields Avenue, Davis, California 95616, USA.
authors.forename: Selina C
authors.initials: SC
authors.lastname: Wang
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo
mesh_terms: D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009930:Organic Chemicals; D012717:Sesquiterpenes; C533354:presilphiperfolanol