An improved synthesis of the "miracle nutrient" coenzyme Q10.
[reaction: see text] A new route to the key coupling partner, chloromethylated CoQ0 (1), allows for direct formation of CoQ10 (3) via nickel-catalyzed cross-coupling with the side chain in the form of an in situ-derived vinyl alane (2).
Lipshutz
Bruce H
BH
Department of Chemistry and Biochemistry, University of California--Santa Barbara, Santa Barbara, California 93106, USA. lipshutz@chem.ucsb.edu
Lower
Asher
A
Berl
Volker
V
Schein
Karin
K
Wetterich
Frank
F
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D000480:Alkynes / Q000737:chemistry; D003067:Coenzymes; D015394:Molecular Structure; D014050:Toluene / Q000031:analogs & derivatives / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry; D014451:Ubiquinone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000475:Alkenes; D000480:Alkynes; D003067:Coenzymes; D014297:Trimethylsilyl Compounds; C022030:methylacetylene; D014451:Ubiquinone; D014050:Toluene; C024989:coenzyme Q10