title: Formal total synthesis of (+/-)-alpha- and beta-cedrene by preparation of cedrone. Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation.
abstract: The cedrene carbon skeleton was rapidly assembled from a simple monocyclic precursor by the strategic use of a high yielding intramolecular Khand cyclization reaction. Further synthetic manipulations provided a concise formal total synthesis of alpha- and beta-cedrene. Reaction: see text.
authors.affiliation: Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, U.K. w.kerr@strath.ac.uk
authors.forename: W J
authors.initials: WJ
authors.lastname: Kerr
authors.forename: M
authors.initials: M
authors.lastname: McLaughlin
authors.forename: A J
authors.initials: AJ
authors.lastname: Morrison
authors.forename: P L
authors.initials: PL
authors.lastname: Pauson
mesh_terms: D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis; D007536:Isomerism; D018653:Juniperus / Q000737:chemistry; D010938:Plant Oils / Q000138:chemical synthesis*; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D010938:Plant Oils; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C000393:cedrene