94828-17-8Relevant articles and documents
A process for the preparation of coenzyme Q10
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Page/Page column 3; 4, (2008/06/13)
A process for the preparation of the compound of formula II by removal of the phenylsulfone group from the compound of formula I characterized in that the phenylsulfone group is removed in the presence of PdCl2-1,2-diphenylphosphinoethane and LiHBEt3.
The Friedel-Crafts allylation of a prenyl group stabilized by a sulfone moiety: Expeditious syntheses of ubiquinones and menaquinones
Min, Jae-Hong,Lee, Jun-Sup,Yang, Jae-Deuk,Koo, Sangho
, p. 7925 - 7927 (2007/10/03)
An efficient synthetic method for the protected p-hydroquinone compounds 4 containing the C5 trans allylic sulfone moiety has been developed by the direct Friedel-Crafts allylation of the protected dihydroquinone 2 with 4-chloro-2-methyl-1-phenylsulfonyl-2-butene (7a) or 4-hydroxy-2-methyl-1-phenylsulfonyl-2-butene (7b). Expeditious total syntheses of coenzyme Q-10 and vitamin K2(20) have been demonstrated from these valuable key compounds 4a and 4b.
Highly S(N)2'-, (E)-, and antiselective alkylation of allylic phosphates. Facile synthesis of coenzyme Q10
Yanagisawa,Nomura,Noritake,Yamamoto
, p. 1130 - 1136 (2007/10/02)
Treatment of secondary allylic chlorides or allylic phosphates in tetrahydrofuran with prenyl Grignard reagent in the presence of CuCN · 2 LiCl gave geraniol or farnesol derivatives with high S(N)2' selectivity. Phosphate leaving groups were highly transstereoselective for the formation of (E,E)-farnesol derivatives. Furthermore, complete anti-S(N)2' selectivity was observed in the alkylation of optically active allylic phosphates. The present method appears to be an excellent carbon-carbon coupling reaction with high regio-, (E)-, and enantioselectivity. Coenzyme Q10 (ubiquinone 10) was efficiently synthesized using this methodology.
Total Synthesis of Linear Polyprenoids. 3. Syntheses of Ubiquinones via Palladium-Catalyzed Oligomerization of Monoterpene Monomers
Eren, Doron,Keinan, Ehud
, p. 4356 - 4362 (2007/10/02)
A general methodology for highly regio- and stereoselective Pd(0)-catalyzed, stepwise allylic coupling of bifunctional monomers was developed, representing a practical approach for total synthesis of naturally occuring polyprenoids.As an example, the total synthesis of the cardiovascular agent ubiquinone 10 (coenzyme Q10), as well as shorter ubiquinones, was carried out via selective coupling of monomers easily derived from geraniol that contain either one or two reacting functional end groups.One of these funcionalities is a latent allylic electrophyle activated by the Pd(0) catalyst and the other is a latent nucleophile activated by an appropriate base.After the desired decaprenyl carbon skeleton of Q10 was achieved, the synthesis was completed by removal of the activating groups: Methyl ester was deleted via a highly efficient demethoxycarbonylation procedure involving 4-aminothiophenol and catalytic amounts of cesium carbonate, and the allylic sulfones were deleted by Pd(0)-catalyzed allylic reduction.Finally, oxidation of the aromatic ring to quinone affords ubiquinone 10.
Synthetic Studies on Isoprenoidquinones. II. Syntheses of Ubiquinone-10, Phylloquinone, and Menaquinone-4 by a Chain-Extending Method Utilizing Terminally Functionalized Isoprenoidhydroquinones
Masaki, Yukio,Hashimoto, Kinji,Kaji, Kenji
, p. 3959 - 3967 (2007/10/02)
Physiologically active polyisopreoidquinones, ubiquinone-10 (coenzyme Q10), phylloquinone (vitamin K1), and menaquinone-4 (vitamin K2(20)) were synthesized by a chain-extending method utilizing protected hydroquinones with the omega-hydroxyprenyl or omega-hydroxygeranyl side chain.Conditions for reductive desulfurization subsequent to allylic homologation was investigated. Keywords - polyisoprenoidquinone synthesis; ubiquinone-10; phylloquinone; menaquinone-4; chain-extending method; sulfone coupling; reductive desulfurization
