- An expeditious route to CoQ(n), Vitamins K1 and K2, and related allylated para-quinones utilizing Ni(0) catalysis
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Coupling reactions between vynylalanes and chloromethylated para-quinones, mediated by catalytic amounts of Ni(0), lead directly to allylated products, including coenzyme Q, and vitamins K1 and K2.
- Lipshutz, Bruce H.,Kim, Sung-Kyu,Mollard, Paul,Stevens, Kirk L.
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p. 1241 - 1253
(2007/10/03)
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- A new synthetic route to ubiquinones
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Ubiquinones 11 have been prepared employing a new strategy: as key step, the Diels-Alder reaction of 1,1,2-trichloroethene 3 with 2,5-bis[(trimethylsilyl)oxy]-3- methylfuran (2) has been used for the construction of the quinone part. After methanolysis of the [4 + 2] adducts 4a/4b, further reaction with cyclopentadiene and substitution of the Cl-atoms by MeO groups, the intermediate 7 is obtained. Diketone 7 can easily be alkylated with the desired polyprenyl side chain 9 (X = Br) using a strong base to yield, after a retro-Diels-Alder reaction, the corresponding ubiquinones 11 in high yields.
- Ruttimann,Lorenz
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p. 790 - 796
(2007/10/02)
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