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    Home > Chen Fener and Peng Haihui of Fudan University constructed the key intermediate of prostaglandin family compounds by enantioselective B-V oxidation catalyzed by chiral spirocyclic phosphonic acid

    Chen Fener and Peng Haihui of Fudan University constructed the key intermediate of prostaglandin family compounds by enantioselective B-V oxidation catalyzed by chiral spirocyclic phosphonic acid

    • Last Update: 2019-09-21
    • Source: Internet
    • Author: User
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    Prostaglandins are a kind of endogenous compounds existing in the body, which have a wide range of physiological functions on endocrine, reproduction, digestion, cardio cerebrovascular and nervous system At present, there are 25 kinds of prostaglandins with different clinical uses on the market, such as prostaglandin (cardiovascular first-line medication), epoprost (pulmonary hypertension first-line medication), latanoprost (anti glaucoma first-line medication), etc However, prostaglandins have few natural sources and are metabolized rapidly in vivo, so chemical synthesis is particularly important The core of its synthesis is to construct a chiral lactone (Corey lactone) with four adjacent stereocenters The production process of Corey lactone with chemical separation as the key step is widely used at home and abroad At most 50% of the required chiral products can be obtained, and 50% of them are industrial wastes Recently, based on the asymmetric Baeyer Villiger (B-V) oxidation catalyzed by chiral spirocyclic phosphonic acid, Chen Fener and Peng Haihui, Department of chemistry, Fudan University, have realized the precise control of high stereoselectivity, developed the green, environmental friendly, efficient and practical asymmetric oxidation reactions without the participation of transition metals, constructed a series of chiral lactones with important physiological activities, and utilized this methodology The key chiral lactone intermediate of prostaglandins was synthesized, and the general asymmetric synthesis of all compounds of prostaglandin family was realized The research results are published online in the international top journal angel Chem Int ed (2019, 58, 9923-9927) under the title of "access to a key building block for the prostaglandin family via stereocontrolled organic Bayer – Villiger oxidation" The key of this study is how to achieve high enantioselectivity B-V oxidation The author cleverly designed a chlorocyclobutanone substrate Through the synergistic activation of cyclobutanone and hydrogen peroxide by chiral spirocyclic phosphonic acid, the conformation of Criegee intermediate in the reaction was effectively controlled, and high enantioselectivity was achieved by high chiral recognition and chiral induction At the same time, chlorocyclobutanone can inhibit the formation of abnormal lactones and realize the kinetic resolution of corresponding normal and abnormal lactones In addition, chlorinated lactones are easy to reduce and dechlorinate to obtain chiral lactones, and the abnormal lactones are dissolved in water and converted into cyclopentene diacid, which is easy to dissolve in water, bringing convenience to post-treatment The research was supported by the National Natural Science Foundation of China (21801042), Shanghai Pujiang Talents Program (18pj1401400) and Fudan University Zhu Kejie, Hu Sha and Liu Minjie of Fudan University are the authors of the paper Academician Chen Fener and young researcher Peng Haihui are the co correspondents of the paper.
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