title: A novel, highly selective, and general methodology for the synthesis of 1,5-diene-containing oligoisoprenoids of all possible geometrical combinations exemplified by an iterative and convergent synthesis of coenzyme Q(10).
abstract: [reaction: see text] A truly general, versatile, and highly regio- and stereoselective methodology for the synthesis of terpenoids containing 1,5-diene units of E and/or Z geometry critically involves Pd-catalyzed homoallyl- and homopropargyl-alkenyl coupling and Zr-catalyzed carboalumination of alkynes. By using this methodology, coenzyme Q(10), (E,Z,E)-geranylgeranoil, and other natural or unnatural compounds have been synthesized efficiently.
authors.affiliation: Herbert C. Brown Laboratories of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA. negishi@purdue.edu
authors.forename: Ei-ichi
authors.initials: E
authors.lastname: Negishi
authors.forename: Show-Yee
authors.initials: SY
authors.lastname: Liou
authors.forename: Caiding
authors.initials: C
authors.lastname: Xu
authors.forename: Shouquan
authors.initials: S
authors.lastname: Huo
mesh_terms: D000480:Alkynes / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*; D014451:Ubiquinone / Q000138:chemical synthesis*; D015040:Zirconium / Q000737:chemistry
chemical_list: D000480:Alkynes; D011090:Polyenes; D013729:Terpenes; D014451:Ubiquinone; D015040:Zirconium