曲古菌素K和L的两种全合成
Two Total Syntheses of Trigoxyphins K and L.
作者信息
Li Shuyang, O'Hanlon Jack A, Mattimoe Andrew, Pickford Helena D, Harwood Lucy A, Wong Luet L, Robertson Jeremy
机构信息
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom.
Department of Chemistry, University of Oxford, Inorganic Chemistry Laboratory, South Parks Road, Oxford OX1 3QR, United Kingdom.
出版信息
Org Lett. 2023 Oct 20;25(41):7507-7511. doi: 10.1021/acs.orglett.3c02796. Epub 2023 Oct 6.
Two total syntheses are presented for trigoxyphins K and L, tricyclic terpenoids from . The first proceeds via electrophlic cyclization in A/C-ring substrates to close the B ring at C4-C5 and then O-mediated hydroxybutenolide formation to trigoxyphin L, with Luche reduction leading to trigoxyphin K. The second route develops from tetralone ring expansion to a B/C-ring intermediate that, by one-step O-demethylation-lactonization-isomerization, affords trigoxyphin K and then trigoxyphin L following enolate oxygenation.
本文介绍了两种从[来源未提及]中提取的三环萜类化合物trigoxyphins K和L的全合成方法。第一种方法是通过A/C环底物中的亲电环化反应在C4-C5处闭合B环，然后通过O介导形成羟基丁烯内酯得到trigoxyphin L，经卢奇还原得到trigoxyphin K。第二种方法是从四氢萘酮扩环生成B/C环中间体，通过一步O-去甲基化-内酯化-异构化反应得到trigoxyphin K，然后烯醇盐氧化得到trigoxyphin L。
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