Preparation of Key Intermediates for the Syntheses of Coenzyme Q10 and Derivatives by Cross-Metathesis Reactions

Trang Nguyen; Hung Mac; Phong Pham

doi:10.3390/molecules25030448

Preparation of Key Intermediates for the Syntheses of Coenzyme Q₁₀ and Derivatives by Cross-Metathesis Reactions

Molecules. 2020 Jan 21;25(3):448. doi: 10.3390/molecules25030448.

Authors

Trang Nguyen¹, Hung Mac², Phong Pham¹

Affiliations

¹ Laboratory of Catalysis at Faculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi 110403, Vietnam.
² Laboratory of Medicinal Chemistry of Faculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi 110403, Vietnam.

Abstract

An alternative catalytic strategy for the preparation of benzylmethacrylate esters, key intermediates in the synthesis of coenzyme Q₁₀ and derivatives, was reported. This strategy avoided undesirable stoichiometric reduction/oxidation processes by utilizing the catalytic formation of allylarenes and then cross-metathesis to selectively form E-benzylmethacrylate esters with good yields (58-64%) and complete E-selectivity. The ester intermediates were reduced to common key benzylallylic alcohols (90-92% yield), which were subsequently used in the formal syntheses of coenzyme Q₁₀ and one derivative.

Keywords: claisen rearrangement; coenzyme Q10; cross-metathesis.; solanesol; stille coupling.

MeSH terms

Benzyl Alcohol / chemistry
Catalysis
Esters / chemical synthesis
Esters / chemistry
Oxidation-Reduction
Ubiquinone / analogs & derivatives*
Ubiquinone / chemical synthesis
Ubiquinone / chemistry

Substances

Esters
Ubiquinone
coenzyme Q10
Benzyl Alcohol

Grants and funding

QG.16.10/Vietnam National University, Hanoi