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Synthetic Studies on Coenzyme Q10. Part 3 : An Improved C5+C45 Approach to the Stereoselective Synthesis of Coenzyme Q10via Metal–Halogen Exchange Strategy

✍ Scribed by Xiong-Jie Yu; Hui-Fang Dai; Fen-Er Chen

Publisher: John Wiley and Sons
Year: 2007
Tongue: German
Weight: 80 KB
Volume: 90
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200790099

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✦ Synopsis

An efficient and stereoselective approach to the synthesis of coenzyme Q 10 is described (Scheme). The MeOCH 2 -protected p-hydroquinone 4 containing the C 5 (E)-allyl (tert-butyl)dimethylsilyl ether moiety was obtained via a halogen -lithium exchange of the MeOCH 2 -proctected 2-bromo-5,6dimethoxy-3-methylhydroquinone 2 and subsequent addition to (E)-( t BuMe 2 Si)-OCH 2 C(Me) ¼ CHCH 2 Br (3). The reductive desulfonylation of compound 8, obtained from 4 via 5 -7, was successfully carried out by employing Li/EtNH 2 .

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Synthetic Studies on Coenzyme Q10. Part

Synthetic Studies on Coenzyme Q10. Part 2 : An Efficient and Improved Synthesis of Coenzyme Q10via the C5 + C45 Approach

✍ Hui-Fang Dai; Fen-Er Chen; Xiong-Jie Yu 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 German ⚖ 76 KB 👁 1 views

An improved route to coenzyme Q 10 (1) starting from commercially available coenzyme Q 1 is described. The key steps in this synthesis are the SeO 2 -mediated oxidation of the protected isoprenylhydroquinone 3 into the (E)-allyl alcohol 5 without the formation of undesired stereoisomer and the one-p