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).
[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.
Negishi
Ei-ichi
E
Herbert C. Brown Laboratories of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA. negishi@purdue.edu
Liou
Show-Yee
SY
Xu
Caiding
C
Huo
Shouquan
S
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
D000480:Alkynes; D011090:Polyenes; D013729:Terpenes; D014451:Ubiquinone; D015040:Zirconium