发明名称 Total synthesis of artemisinin
摘要 The present invention provides a method for manufacturing artemisinin and its congeners from cyclohexenone as a starting material.;
申请公布号 US9035077(B2) 申请公布日期 2015.05.19
申请号 US201214114748 申请日期 2012.05.10
申请人 Indiana University Research & Technology Corporation 发明人 Cook Silas;Zhu Chun-Yin
分类号 C07D493/16;C07D493/18 主分类号 C07D493/16
代理机构 Klintworth & Rozenblat IP LLC 代理人 Klintworth & Rozenblat IP LLC
主权项 1. A method for manufacturing molecules of Formula F: the method comprising the steps of: reacting a first mixture comprising cyclohexenone, an alkylating agent and a methyl vinyl ketone (MVK) equivalent to form a first synthetic intermediate of Formula B: wherein R1 is an alkyl moiety and moiety Y is a moiety derived from the MVK equivalent and that can be converted subsequently to a —CH2CH2C(O)CH3 moiety; reacting a second mixture comprising the intermediate of Formula B and a formylating agent under basic conditions to form an aldehyde intermediate of Formula C: reacting a third mixture comprising the intermediate of Formula C and a dienophile under [4+2] reaction conditions to form an intermediate of Formula D: wherein: R2 is selected from the group consisting of —H, alkyl, cycloalkyl, heterocycle, and aryl, and X1 and X2 are independently selected from the group consisting of —H, —OH, —OCH3, —OCH2CH3, —OSiR′, —OR″, wherein R′ is alkyl and R″ is alkyl, or X1 and X2 together form an oxo; reacting a fourth mixture comprising intermediate D and an MVK converting agent to form an intermediate of Formula E:wherein the MVK converting agent reacts with the moiety Y of compound D to convert moiety Y to a —CH2CH2C(O)CH3 moiety; and reacting a fifth mixture comprising the intermediate of Formula E, hydrogen peroxide and a metal catalyst to form molecules of Formula F.
地址 Indianapolis IN US
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