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.
Highlights
Coenzyme Q10 (1), an isoprenylated quinone, is a critical electron-transfer compound found in all respiring eukaryotic cells [1,2,3]
The frame of coenzyme Q10 can be viewed as a combination of terpenyl and aromatic fragments
This strategy served as the framework for the synthesis of coenzyme Q10 based on the terpenyl chain from solanesol
Summary
Coenzyme Q10 (1), an isoprenylated quinone, is a critical electron-transfer compound found in all respiring eukaryotic cells [1,2,3]. Alcohol (2c) was used in transformations with the solanesyl bromide obtained from the bromination of solanesol to achieve coenzyme Q10 (Scheme 1). This strategy served as the framework for the synthesis of coenzyme Q10 based on the terpenyl chain from solanesol. A similar unexpected oxidation was observed by the Hecht group [12] This result led to an undesirable stoichiometric reduction step being added to the synthesis. The iso-pentenylated quinol was stoichiometrically oxidized by SeO2 to aldehyde, not alcohol, and required an extra reduction step to obtain the benzylallyl alcohol (2c). A previous stoichiometric approach to coenzyme Q10 through benzylallyl alcohol (2c)
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