Ein neuer synthetischer Zugang zu Ubichinonen

✍ Scribed by August Rüttimann; Peter Lorenz

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: German
• Weight: 460 KB
• Volume: 73
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19900730404

✦ Synopsis

A New Synthetic Route to Ubiquinones

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 + 21 adducts 4a/4b, further reaction with cyclopentadiene and substitution of the C1-atoms by Me0 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.