82349-09-5Relevant articles and documents
Synthetic studies on coenzyme Q10: Part 1 - An efficient and highly stereocontrolled synthesis of coenzyme Q10 via a C 5+C45 strategy
Yu, Xiong-Jie,Chen, Fen-Er,Dai, Hui-Fang,Chen, Xu-Xiang,Kuang, Yun-Yan,Xie, Bin
, p. 2575 - 2581 (2007/10/03)
A practical, highly stereoselective ten-step synthesis of coenzyme Q 10 (1) has been accomplished (overall yield ca. 28%), starting from commercially available 2,3-dimethoxy-5-methylbenzoquinone (Scheme). The introduction of the first side-chain isoprenyl group with (E)-configuration (compound 6) was realized by means of a coupling reaction of the aromatic system 3 with oxirane, followed by Swern oxidation and Wittig olefination. The tosyl (Ts) group in the sulfone 9 was selectively removed with sodium naphthalenide in THF to afford 1.