國家衛生研究院 NHRI:Item 3990099045/14462
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    Please use this identifier to cite or link to this item: http://ir.nhri.org.tw/handle/3990099045/14462


    Title: Recent advances in total synthesis of natural products by masked ortho-benzoquinones
    Authors: Chen, CM;Hsieh, HP
    Contributors: Institute of Biotechnology and Pharmaceutical Research
    Abstract: The Diels-Alder adducts of masked ortho-benzoquinone (MOB) normally perform high regio- and stereoselectivity and are generated under mild conditions. The advantages of MOB include: (a) Containing highly functional moieties: alkene, diene, carbonyl, enone, and dienone; (b) Easily accessible from 2-methoxyphenol derivatives via oxidative dearomatization, and related 2-methoxyphenol easily prepared from commercially available starting materials; (c) The Diels-Alder adducts possessing unique features such as regio- and stereoselectivity and at least four contiguous stereogenic centers in one step. Furthermore, related bicyclo[2.2.2]octenone skeleton can be applied to further complex structure construction by various chemical transformations, such as radical cyclization, oxa-di-pi-methane rearrangement, Beckwith-Dowd rearrangement, hydrogen atom transfer reaction, Cope rearrangement, Wanger-Meerwein rearrangement, carbonyl-ene reaction, aldol reaction, ring opening etc. Among these advantages, MOB system is prospected to continue as an important intermediate for total synthesis of natural products.
    Date: 2022-08-09
    Relation: Journal of the Chinese Chemical Society. 2022 Aug 09;69(8):1210-1222.
    Link to: http://dx.doi.org/10.1002/jccs.202200276
    JIF/Ranking 2023: http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=NHRI&SrcApp=NHRI_IR&KeyISSN=0009-4536&DestApp=IC2JCR
    Cited Times(WOS): https://www.webofscience.com/wos/woscc/full-record/WOS:000837903000001
    Cited Times(Scopus): https://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85135751677
    Appears in Collections:[Hsing-Pang Hsieh] Periodical Articles

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